tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate

Base Information

• Chemical Name: tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate
• CAS No.: 1609959-50-3
• Molecular Formula: C₂₃H₃₄N₂O₅
• Molecular Weight: 418.533

Synonyms:tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate

Chemical Property of tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate

There total 7 articles about tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (14676-01-8) + (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one (247068-84-4) → tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate (1609959-50-3)

Guidance literature:

3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 0.5h;

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h;

DOI:10.1016/j.bmc.2014.04.011

Reference yield:

tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate (247068-81-1) → tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate (1609959-50-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C

3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C

5.2: 3 h

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmc.2014.04.011

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate (1609959-50-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C

1.2: 3 h / 0 °C

2.1: tetrahydrofuran / 0 °C / Inert atmosphere

3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C

5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C

7.2: 3 h

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmc.2014.04.011

upstream raw materials:

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

N-tert-butoxycarbonyl-L-leucine

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

tert-butyl N-[(4S)-3-hydroxy-2,6-dimethylhept-1-en-4-yl]carbamate

Downstream raw materials:

C₁₈H₂₆N₂O₃

tert-butyl (1S)-4-methyl-1-{3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylamino}-1-oxopentan-2-ylcarbamate

tert-butyl (1S)-1-{3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylamino}-1-oxo-3-phenylpropan-2-ylcarbamate

N-{(2S)-4-methyl-1-{3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylamino}-1-oxopentan-2-yl}pyrazine-2-carboxamide

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