Potassium Carbonate → HCID 12812615, compound

HRID 2413182Notes

Reaction equation

HRID 2413182 reaction equation
[SH:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][S:8][CH2:7]1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:21]1([C:27](Cl)=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>O>[CH:21]1([C:27]([S:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]2[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][S:8][CH2:7]2)=[O:5])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75938Cyclohexanecarbonyl chlorideHCID 171857YS 980

Product 1

HCID 12812615HCID 12812615, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.4 g of (4R)-3-[(2S)-3-mercapto-2-methylpropanoyl]-4-thiazolidinecarboxylic acid and 2.8 g of potassium carbonate are dissolved in 50 ml of water. To this solution, 1.8 g of cyclohexanecarbonyl 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. This reaction solution is washed with ethyl acetate, acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give oil, yield 3.5 g. The oil is purified by silica gel column chromatography to give the titled compound, yield 2.8 g (81%), mp. 79.5°-80° C. (benzene-n-hexane), [α]D23 -176.2° (c=1.0, methanol).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. washThis reaction solution is washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give oil, yield 3.5 g
  10. customThe oil is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-720946ac421145a291adb123683a5013
Source dataset
uspto-grants-1985_01
Patent number
US04496578

Reaction notes

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