Potassium Carbonate → HCID 12813282, compound

HRID 1979922Notes

Reaction equation

HRID 1979922 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[NH:15][C@H:14]([C:16]([OH:18])=[O:17])[CH2:13][S:12]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:25]([S:28][CH2:29][CH2:30][C:31](Cl)=[O:32])(=[O:27])[CH3:26]>O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[N:15]([C:31](=[O:32])[CH2:30][CH2:29][S:28][C:25](=[O:27])[CH3:26])[C@H:14]([C:16]([OH:18])=[O:17])[CH2:13][S:12]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 53998704HCID 53998704, compound

Product 1

HCID 12813282HCID 12813282, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.7 g of (4R)-2-(2-acetoxyphenyl)-4-thiazolidinecarboxylic acid and 2.8 g of potassium carbonate are dissolved in 60 ml of water. To this solution, 1.8 g of S-acetyl-3-mercaptopropanoyl 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 2.8 g (70%), mp. 144°-145° C. (ethyl acetate-benzene), [α]D27 +109.0° (c=1.0, 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 2.8 g (70%), mp. 144°-145° C. (ethyl acetate-benzene), [α]D27 +109.0° (c=1.0, methanol)

Sources & evidence

ORD record
ord-c707599e94994534a2936dcd50716f37
Source dataset
uspto-grants-1984_11
Patent number
US04483861

Reaction notes

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