Hydrochloric Acid → (S)-4-azido-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline

Reaction equation

[N:1]([CH:4]1[CH2:8][N:7]([C:9](=[O:24])[CH2:10][P:11]([OH:23])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[C@H:6]([C:25]([O:27]C)=[O:26])[CH2:5]1)=[N+:2]=[N-:3].[OH-].[Na+].Cl>>[N:1]([CH:4]1[CH2:8][N:7]([C:9](=[O:24])[CH2:10][P:11]([OH:23])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[C@H:6]([C:25]([OH:27])=[O:26])[CH2:5]1)=[N+:2]=[N-:3]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 131712759(S)-4-Azido-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester

Product 1

HCID 86738870(S)-4-azido-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-prolineYield 88.4%

Procedure

(S)-4-Azido-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester (1.30 g) and 1 N sodium hydroxide (about 15 ml) is stirred for 30 minutes. The reaction mixture is acidified with concentrated hydrochloric acid, extracted with ethyl acetate, washed with water, washed with brine, dried over sodium sulfate, and the solvent is stripped yielding 1.11 g of the title compound having an optical rotation [α]D =-22.3° (c=10 mg/ml, methanol). The product contains 1/2 mole of water.