Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]1.C(N(CC)CC)C.[C:23]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28][S:27][S:26][CH2:25][CH2:24]1>CC(C)=O>[C:23]([CH2:24][CH2:25][S:26][S:27][CH2:28][CH2:29][C:30]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])=[O:31])([OH:33])=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2.0 g of (4R)-2-hydroxyphenyl-4-thiazolidinecarboxylic acid and 1.7 ml of triethylamine in 15 ml of anhydrous acetone, 2.0 g of dithiodipropanoic anhydride is added. The resulting mixture is continuously stirred for 40 min at room temperature and extracted with ethyl acetate after addition of 50 ml of water containing a small amount of potassium carbonate. The aqueous layer is acidified with N aqueous hydrochloric acid and extracted with ethyl acetate. The second organic layer is washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residual oil is purified by column chromatography on silica gel to give crystals of the titled compound. The yield is 0.6 g (15%).
Workup
- extractionextracted with ethyl acetate
- additionafter addition of 50 ml of water containing a small amount of potassium carbonate
- extractionextracted with ethyl acetate
- washThe second organic layer is washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residual oil is purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-cbdce532f20e489e8803e3a261262509
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04347371
Linked notes
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