tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS No.: 1469983-01-4
• Molecular Formula: C₂₃H₃₄N₂O₅
• Molecular Weight: 418.533

Synonyms:tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property of tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property:

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Technology Process of tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

There total 7 articles about tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 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: 87.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one (247068-84-4) → tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1469983-01-4)

Guidance literature:

N-tert-butoxycarbonyl-L-phenylalanine; 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 ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1469983-01-4)

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 ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1469983-01-4)

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-phenylalanine

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

N-tert-butoxycarbonyl-L-leucine

Downstream raw materials:

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

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

N-{3-{(2S)-1-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-1-oxo-3-phenylpropan-2-ylamino}-3-oxo-1-phenylpropyl}-tetrahydro-2H-pyran-4-carboxamide

1-acetyl-N-{3-{(2S)-1-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-1-oxo-3-phenylpropan-2-ylamino}-3-oxo-1-phenylpropyl}piperidine-4-carboxamide

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