methyl (3S)-4-amino-3-hydroxybutanoate hydrochloride → (S)-4-((S)-2-Hydroxy-3-methoxycarbonyl-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 2095496Notes

Reaction equation

HRID 2095496 reaction equation
CO[C:3](=[O:20])[C@@H:4]([N:6]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:7][CH:8]=O)[CH3:5].Cl.[CH3:22][O:23][C:24](=[O:30])[CH2:25][C@H:26]([OH:29])[CH2:27][NH2:28]>>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][N:28]([CH2:27][C@@H:26]([OH:29])[CH2:25][C:24]([O:23][CH3:22])=[O:30])[C:3](=[O:20])[C@@H:4]1[CH3:5])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 9898943methyl (3S)-4-amino-3-hydroxybutanoate hydrochloride2×HCID 86638111(S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester2×

Product 1

HCID 67074026(S)-4-((S)-2-Hydroxy-3-methoxycarbonyl-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl esterYield 59%

Procedure

In analogy to the procedure described in Example 12D, (S)-2-[benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester (intermediate 12C) and (S)-4-amino-3-hydroxy-butyric acid methyl ester, hydrochloride (intermediate 24) gave the titled compound in 59% yield as light yellow oil. MS: 365.17 (MH+).

Sources & evidence

ORD record
ord-abfa3ea669a84058b85772c6661c4c10
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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