Sodium Hydroxide → HCID 13136852, compound

HRID 1156799Notes

Reaction equation

HRID 1156799 reaction equation
[OH:1][P:2]([CH2:14][C:15]([N:17]1[C@H:25]([C:26]([O:28]C)=[O:27])[CH2:24][C:19]2([S:23][CH2:22][CH2:21][S:20]2)[CH2:18]1)=[O:16])([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:3].[OH-].[Na+]>>[OH:3][P:2]([CH2:14][C:15]([N:17]1[C@H:25]([C:26]([OH:28])=[O:27])[CH2:24][C:19]2([S:20][CH2:21][CH2:22][S:23]2)[CH2:18]1)=[O:16])([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:1]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 14103105HCID 14103105, compound

Product 1

HCID 13136852HCID 13136852, compoundYield 94.5%

Procedure

(S)-7-[[Hydroxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, methyl ester (2.99 g) and 1 N sodium hydroxide (15 ml) is stirred for 30 minutes at room temperature. The reaction mixture is extracted with ether (50 ml) and the aqueous phase is acidified with concentrated hydrochloric acid to pH 1.0. A solid precipitates out of solution along with an oil. This is extracted into ethyl acetate, passed through sodium sulfate, and the solvent is stripped yielding 2.74 g of the title compound, melting point 105.5°-107° C.

Workup

  1. extractionThe reaction mixture is extracted with ether (50 ml)
  2. customA solid precipitates out of solution along with an oil
  3. extractionThis is extracted into ethyl acetate

Sources & evidence

ORD record
ord-c6125e3a879442559417df1eb80204d9
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

Loading…