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

HRID 851431Notes

Reaction equation

HRID 851431 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-6ca81c1e9af947baa4ea74f4d2f461f2
Source dataset
uspto-grants-1983_05
Patent number
US04384123

Reaction notes

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