(S)-2-amino-4-benzyloxy-butyric acid methyl ester hydrochloride → (S)-4-Benzyloxy-2-{(R)-2-[benzyloxycarbonyl-(2-tert-butoxycarbonyl-ethyl)-amino]-propylamino}-butyric acid methyl ester

HRID 655568Notes

Reaction equation

HRID 655568 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][N:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:10]([CH3:13])[CH:11]=O)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:26][O:27][C:28](=[O:41])[C@@H:29]([NH2:40])[CH2:30][CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH3:26][O:27][C:28](=[O:41])[C@@H:29]([NH:40][CH2:11][C@H:10]([N:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])[CH3:13])[CH2:30][CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 66782906(S)-2-amino-4-benzyloxy-butyric acid methyl ester hydrochloride2×HCID 866381153-[benzyloxycarbonyl-((R)-1-methyl-2-oxo-ethyl)-amino]-propionic acid tert-butyl ester

Product 1

HCID 67079859(S)-4-Benzyloxy-2-{(R)-2-[benzyloxycarbonyl-(2-tert-butoxycarbonyl-ethyl)-amino]-propylamino}-butyric acid methyl ester

Procedure

In analogy to the procedure described in example 58D, 3-[benzyloxycarbonyl-((R)-1-methyl-2-oxo-ethyl)-amino]-propionic acid tert-butyl ester and (S)-2-amino-4-benzyloxy-butyric acid methyl ester hydrochloride (intermediate 7) gave the title compound in quantitative yield as yellow oil. MS: 543.5 (MH+).

Sources & evidence

ORD record
ord-42332118bb1a4392a3bc84606a9cd7f8
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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