Sodium Hydroxide → HCID 13136852, compound

HRID 851427Notes

Reaction equation

HRID 851427 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, compound

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 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-74a52d67aecc46ccb83f9199df753e28
Source dataset
uspto-grants-1983_05
Patent number
US04384123

Reaction notes

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