Ammonium Hydroxide → 2-(3-Mercapto-1-oxopropyl)-5-oxo-3-pyrazolidinecarboxylic acid

HRID 27261Notes

Reaction equation

HRID 27261 reaction equation
C([S:4][CH2:5][CH2:6][C:7]([N:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11](=[O:17])[NH:10]1)=[O:8])(=O)C.[OH-].[NH4+]>>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11](=[O:17])[NH:10]1)=[O:8]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 23344444HCID 23344444, compound

Product 1

HCID 233444412-(3-Mercapto-1-oxopropyl)-5-oxo-3-pyrazolidinecarboxylic acidYield 44.7%

Procedure

DL-2-[3-(Acetylthio)-1-oxopropyl]-5-oxo-3-pyrazolidinecarboxylic acid (1.2 g) is treated in an argon atmosphere with 8 ml of a cold solution of 6.5 N ammonium hydroxide. After one hour at room temperature, the solution is extracted with ethyl acetate and treated with concentrated hydrochloric acid to pH 2. The water soluble product is extracted with five 20 ml portions of ethyl acetate. The combined extracts are dried over magnesium sulfate and evaporated to an oil which gradually solidifies. This material is dried in vacuo at 100° C. for 1 hour yielding 0.45 g of the title compound, melting point 140°-142° C.

Workup

  1. extractionthe solution is extracted with ethyl acetate
  2. additiontreated with concentrated hydrochloric acid to pH 2
  3. extractionThe water soluble product is extracted with five 20 ml portions of ethyl acetate
  4. dry with materialThe combined extracts are dried over magnesium sulfate
  5. customevaporated to an oil which
  6. customThis material is dried in vacuo at 100° C. for 1 hour

Sources & evidence

ORD record
ord-39f6373776314ee2a372f4309ef8097e
Source dataset
uspto-grants-1980_09
Patent number
US04220791

Reaction notes

Loading…