Penicillamine → 2,5,5-Trimethyl-2-[2-oxo-2-(pyrrolidin-1-yl)ethyl]-1,3-thiazolidine-4-carboxylic acid
Reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]=[C:7]1O[C:9](=[O:10])[CH2:8]1.[NH2:12][C@@H:13]([C:18]([OH:20])=[O:19])[C:14]([SH:17])([CH3:16])[CH3:15]>C1C=CC=CC=1>[CH3:15][C:14]1([CH3:16])[S:17][C:7]([CH2:8][C:9]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:10])([CH3:6])[NH:12][CH:13]1[C:18]([OH:20])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3.6 g (50 mmoles) of pyrrolidine in 50 mg of anhydrous benzene was added dropwise a solution of 4.2 g (50 mmoles) of diketene in 50 ml of anhydrous benzene at 0°-5° C. over 2 hours. The mixture was allowed to stand at room temperature for 2 hours, and the solvent was distilled off to a half its volume under reduced pressure. To the residue was added 5 g (34 mmoles) of D-penicillamine. The mixture was heated at 80° C. with stirring under a stream of argon for an hour to obtain a pale yellow and clear reaction mixture. The reaction mixture was filtered, the solvent was distilled off and the resulting residue was washed with a mixture of n-hexane and ether. The viscous residue thus obtained was crystallized from hot benzene and further recrystallized from benzene to give 9.5 g of 4-carboxy-2,5,5-trimethylthiazolidine-2-acetopyrrolidide as colorless prisms.
Workup
- distillationthe solvent was distilled off to a half its volume under reduced pressure
- customto obtain a pale yellow and clear reaction mixture
- filtrationThe reaction mixture was filtered
- distillationthe solvent was distilled off
- washthe resulting residue was washed with a mixture of n-hexane and ether
- customThe viscous residue thus obtained
- customwas crystallized from hot benzene
- customfurther recrystallized from benzene
Sources & evidence
- ORD record
- ord-46f5cd56efa74303a6f1f1429b2404b5
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04398026
Reaction notes
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