Potassium Carbonate → HCID 12813290, compound

HRID 2413181Notes

Reaction equation

HRID 2413181 reaction equation
[SH:1][C@@H:2]([CH3:13])[C:3]([N:5]1[C@H:9]([C:10]([OH:12])=[O:11])[CH2:8][S:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:20]1([CH3:29])[CH:25]=[CH:24][C:23]([C:26](Cl)=[O:27])=[CH:22][CH:21]=1>O>[CH3:29][C:20]1[CH:25]=[CH:24][C:23]([C:26]([S:1][C@@H:2]([CH3:13])[C:3]([N:5]2[C@H:9]([C:10]([OH:12])=[O:11])[CH2:8][S:7][CH2:6]2)=[O:4])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 134054-Methylbenzoyl ChlorideHCID 1549934-Thiazolidinecarboxylic acid, 3-(2-mercapto-1-oxopropyl)-, (S-(R*,S*))-

Product 1

HCID 12813290HCID 12813290, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.2 g of (4R)-3-[(2S)-2-mercaptopropanoyl]-4-thiazolidinecarboxylic acid and 2.8 g of potassium carbonate are dissolved in 50 ml of water. To this solution, 1.6 g of p-toluoyl chloride is added dropwise with stirring under ice-cooling. After the addition, the mixture is stirred under ice-cooling for 1 hour and at room temperature for additional 1 hour. The reaction solution is washed with ethyl acetate, and acidified with conc. hydrochloric acid to give crystals. The crystals (the titled compound) are collected by filtration, yield 3.3 g (97%), mp. 166°-166.5° C. (ethyl acetate), [α]D25 -148.6° (c=1.1, methanol).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. washThe reaction solution is washed with ethyl acetate
  5. customto give crystals
  6. filtrationThe crystals (the titled compound) are collected by filtration, yield 3.3 g (97%), mp. 166°-166.5° C. (ethyl acetate), [α]D25 -148.6° (c=1.1, methanol)

Sources & evidence

ORD record
ord-42ae84dd839d4bcdbb91fb83ce7334f9
Source dataset
uspto-grants-1985_01
Patent number
US04496578

Reaction notes

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