(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester

Base Information

• Chemical Name: (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester
• CAS No.: 158009-27-9
• Molecular Formula: C₂₅H₃₃ClN₂O₇
• Molecular Weight: 508.999

Synonyms:(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester

Chemical Property of (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester

Chemical Property:

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Technology Process of (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester

There total 4 articles about (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester 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: 54.0%

(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R,4S/R)-3-chloro-4-hydroxy-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester → (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester (158009-27-9)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 23 ℃; for 4h;

DOI:10.1021/jo00089a019

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester (158009-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylamine / dimethylformamide / 18 h / 23 °C

2: 54 percent / MnO₂ / CH₂Cl₂ / 4 h / 23 °C

With manganese(IV) oxide; N-cyclohexyl-cyclohexanamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00089a019

Reference yield:

(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R,4S/R)-3-chloro-4-hydroxy-2-cyclohexen-1-yl>alanine methyl ester (137232-95-2,137331-07-8) → (S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R)-3-chloro-4-oxo-2-cyclohexen-1-yl>alanine p-methoxybenzyl ester (158009-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.1 N aq. NaOH / tetrahydrofuran / 0.5 h / 23 °C

2: dicyclohexylamine / dimethylformamide / 18 h / 23 °C

3: 54 percent / MnO₂ / CH₂Cl₂ / 4 h / 23 °C

With manganese(IV) oxide; sodium hydroxide; N-cyclohexyl-cyclohexanamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00089a019

upstream raw materials:

p-Methoxybenzyl bromide

(S)-(tert-Butyloxycarbonyl)alanyl-(S)-3-<(1R,4S/R)-3-chloro-4-hydroxy-2-cyclohexen-1-yl>alanine methyl ester

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