Potassium Carbonate → HCID 12813336, compound

HRID 1979923Notes

Reaction equation

HRID 1979923 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+].[CH3:25][C:26]1[CH:39]=[CH:38][C:29]([C:30]([S:32][CH2:33][CH2:34][C:35](Cl)=[O:36])=[O:31])=[CH:28][CH:27]=1>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:35](=[O:36])[CH2:34][CH2:33][S:32][C:30](=[O:31])[C:29]2[CH:38]=[CH:39][C:26]([CH3:25])=[CH:27][CH:28]=2)[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 53998704HCID 53998704, compoundHCID 86739765HCID 86739765, compound

Product 1

HCID 12813336HCID 12813336, 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, 2.6 g of S-(4-methylbenzoyl)-3-mercaptopropanoyl chloride is added dropwise with stirring under icecooling. After the addition, the mixture is stirred under icecooling 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 3.6 g. The oil is purified by silica gel column chromatography to give the titled compound, yield 2.7 g (57%), mp. 93°-96° C. (benzene). [α]D24 +80.4° (c=1.0, methanol).

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred
  3. washThis reaction solution is washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give oil, yield 3.6 g
  9. customThe oil is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f509488e85834c65b274ab15b9de612b
Source dataset
uspto-grants-1984_11
Patent number
US04483861

Reaction notes

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