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247068-82-2

  • Product Name:CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester
  • Molecular Formula:C14H25NO4
  • Molecular Weight:271.357
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Product Details

Purity:99%

High Quality Chinese Manufacturer supply 247068-82-2 CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester

  • Molecular Formula:C14H25NO4
  • Molecular Weight:271.357
  • Boiling Point:369.8±37.0 °C(Predicted) 
  • PKA:11.08±0.46(Predicted) 
  • PSA:67.93000 
  • Density:1.061±0.06 g/cm3(Predicted) 
  • LogP:2.67470 

247068-82-2 Relevant articles

Bioinspired manganese complexes catalyzed epoxidation for the synthesis of the epoxyketone fragment of carfilzomib

Qiu, Bin,Xia, Chungu,Sun, Wei

, p. 698 - 701 (2019)

We report herein an efficient catalytic ...

Continuous Process Improvement in the Manufacture of Carfilzomib, Part 2: An Improved Process for Synthesis of the Epoxyketone Warhead

Beaver, Matthew G.,Shi, Xianqing,Riedel, Jan,Patel, Parth,Zeng, Alicia,Corbett, Michael T.,Robinson, Jo Anna,Parsons, Andrew T.,Cui, Sheng,Baucom, Kyle,Lovette, Michael A.,I?ten, El?in,Brown, Derek B.,Allian, Ayman,Flick, Tawnya G.,Chen, Wendy,Yang, Ning,Walker, Shawn D.

, p. 490 - 499 (2020)

The development and kilogram-scale demon...

Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer's Disease

Lee, Min Jae,Bhattarai, Deepak,Jang, Hyeryung,Baek, Ahreum,Yeo, In Jun,Lee, Seongsoo,Miller, Zachary,Lee, Sukyeong,Hong, Jin Tae,Kim, Dong-Eun,Lee, Wooin,Kim, Kyung Bo

, p. 10934 - 10950 (2021/08/20)

Previously, we reported that immunoprote...

Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline

Lin, Jin,Sun, Wei,Tian, Jing,Xia, Chungu,Zhang, Jisheng

supporting information, (2021/11/16)

A family of manganese complexes [Mn(Rpeb...

LMP2 Inhibitors as a Potential Treatment for Alzheimer's Disease

Bhattarai, Deepak,Lee, Min Jae,Baek, Ahruem,Yeo, In Jun,Miller, Zachary,Baek, Yu Mi,Lee, Sukyeong,Kim, Dong-Eun,Hong, Jin Tae,Kim, Kyung Bo

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The immunoproteasome (iP), an inducible ...

Continuous Process Improvement in the Manufacture of Carfilzomib, Part 1: Process Understanding and Improvements in the Commercial Route to Prepare the Epoxyketone Warhead

Dornan, Peter K.,Anthoine, Travis,Beaver, Matthew G.,Cheng, Guilong Charles,Cohen, Dawn E.,Cui, Sheng,Lake, William E.,Langille, Neil F.,Lucas, Susan P.,Patel, Jenil,Powazinik, William,Roberts, Scott W.,Scardino, Chris,Tucker, John L.,Spada, Simone,Zeng, Alicia,Walker, Shawn D.

, p. 481 - 489 (2020/04/10)

Epoxyketone 4 is an isolated intermediat...

247068-82-2 Process route

tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate
247068-81-1

tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
247068-82-2,247068-83-3

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions
Conditions Yield
With (R)-La-BINOL; triphenylphosphine; tert-butyl alcohol; In toluene; at 20 ℃; for 0.5h; Solvent;
85%
With dihydrogen peroxide; benzonitrile; N-ethyl-N,N-diisopropylamine; In methanol; at 0 ℃;
57%
With dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In methanol; benzonitrile; at 0 ℃; for 3h; Inert atmosphere;
57%
With tetramethyl ammoniumhydroxide; urea hydrogen peroxide adduct; In methanol; benzonitrile; at -10 ℃; for 20h; Reagent/catalyst; Solvent; stereoselective reaction; Inert atmosphere;
40%
With potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate; In water; acetonitrile; diastereoselective reaction; Inert atmosphere;
26%
tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate; With sodium hydrogencarbonate;
With Oxone; In water; acetonitrile; at -10 ℃; for 1h;
26%
With 1,1,1-trifluoro-2-propanone; oxone||potassium monopersulfate triple salt; sodium hydrogencarbonate; In water; at -10 ℃; for 1.5h;
26%
With dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In methanol; for 2h;
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
3: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
With sodium tetrahydroborate; cerium(III) chloride heptahydrate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.08 h / 0 °C / Inert atmosphere
2: bis(acetylacetonate)oxovanadium; tert.-butylhydroperoxide / dichloromethane / 1 h / 0 °C / Inert atmosphere
3: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / Inert atmosphere
With tert.-butylhydroperoxide; sodium tetrahydroborate; bis(acetylacetonate)oxovanadium; cerium(III) chloride heptahydrate; Dess-Martin periodane; In methanol; dichloromethane; 2: |Sharpless Asymmetric Epoxidation / 3: |Dess-Martin Oxidation;
With Oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate; In water; acetonitrile; at -10 ℃; for 1.5h; Inert atmosphere;
Multi-step reaction with 3 steps
1: aluminum isopropoxide; isopropyl alcohol / toluene / 50 °C / Green chemistry
2: vanadium trisacetylacetonate; tert.-butylhydroperoxide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere; Green chemistry
3: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 20 °C / Green chemistry
With tert.-butylhydroperoxide; vanadium trisacetylacetonate; sulfur trioxide pyridine complex; aluminum isopropoxide; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; In dichloromethane; dimethyl sulfoxide; toluene;
With calcium hypochlorite; In 1-methyl-pyrrolidin-2-one; water; at -15 - 0 ℃; for 0.333333h;
20.8 g
With dihydrogen peroxide; potassium carbonate; benzonitrile; In methanol; at 25 - 30 ℃; for 6h;
16.5 g
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 1 h / 0 - 5 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 30 °C
3: Dess-Martin periodane / acetonitrile / 3 h / 0 - 30 °C
With sodium tetrahydroborate; cerium(III) chloride heptahydrate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; acetonitrile;
Multi-step reaction with 3 steps
1: aluminum isopropoxide / toluene; isopropyl alcohol / 20 - 50 °C
2: bis(acetylacetonate)oxovanadium; tert.-butylhydroperoxide / dichloromethane / 0 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 20 °C / Cooling with ice
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; sulfur trioxide pyridine complex; aluminum isopropoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; isopropyl alcohol; toluene;
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.42 h / 0 °C
2: bis(acetylacetonate)oxovanadium; tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C
3: Dess-Martin periodane / dichloromethane / 20 °C
With tert.-butylhydroperoxide; sodium tetrahydroborate; bis(acetylacetonate)oxovanadium; cerium(III) chloride heptahydrate; Dess-Martin periodane; In methanol; dichloromethane;
Multi-step reaction with 3 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / 0 °C / Inert atmosphere
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
3: Dess-Martin periodane / dichloromethane / 10 h / 0 °C / Inert atmosphere
With sodium tetrahydroborate; cerium(III) chloride heptahydrate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 3 steps
1: aluminum isopropoxide; isopropyl alcohol / toluene / 3 h / 50 °C
2: tert.-butylhydroperoxide; tris(acetylacetonato)vanadium(III) / dichloromethane / 12 h / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 6 h
With tert.-butylhydroperoxide; tris(acetylacetonato)vanadium(III); sulfur trioxide pyridine complex; aluminum isopropoxide; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; In dichloromethane; dimethyl sulfoxide; toluene;
With pyridine; sodium hypochlorite; In water; at -15 - -5 ℃; for 4.75h;
284 g
tert-butyl {(1S,2S)-1-hydroxy-4-methyl-1-[(R)-2-methyloxiran-2-yl]pentan-2-yl}carbamate

tert-butyl {(1S,2S)-1-hydroxy-4-methyl-1-[(R)-2-methyloxiran-2-yl]pentan-2-yl}carbamate

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
247068-82-2,247068-83-3

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

Conditions
Conditions Yield
With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 ℃; Green chemistry;
91%
With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 ℃; Cooling with ice;
83.3%
With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;
46%
With sodium hypochlorite; 2-azatricyclo[3.3.1.13,7]decan-2-ol; sodium hydrogencarbonate; In water; toluene; at 0 ℃; for 5h;
5.96 g
With Dess-Martin periodane; In dichloromethane; at 20 ℃;

247068-82-2 Upstream products

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247068-82-2 Downstream products

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