Acetone → 2,2,5,5-Tetramethyl-1,3-thiazolidine-4-carboxylic acid

Reaction equation

Cl.[NH2:2][CH:3]([C:8]([OH:10])=[O:9])[C:4]([SH:7])([CH3:6])[CH3:5].[CH3:11][C:12]([CH3:14])=O>>[CH3:5][C:4]1([CH3:6])[S:7][C:12]([CH3:14])([CH3:11])[NH:2][CH:3]1[C:8]([OH:10])=[O:9]

Participants

Reactant 2

HCID 180Acetone

HCID 12278514dl-Valine, 3-mercapto-, hydrochloride

Product 1

HCID 939642,2,5,5-Tetramethyl-1,3-thiazolidine-4-carboxylic acid

Procedure

Ninety-three grams (0.5 mole) of D,L-penicillamine hydrochloride in 500 ml of acetone were heated at reflux temperature for 30 minutes under a nitrogen atmosphere. After distilling off the excess acetone there were obtained 113 grams of D,L-2,2,5,5-tetramethyl-thiazolidine-4-carboxylic acid. The yield amounts to 99%.

Workup

temperatureat reflux temperature for 30 minutes under a nitrogen atmosphere
distillationAfter distilling off the excess acetone there

Sources & evidence

ORD record: ord-d3810b3d329845aaab5dab9d9c145918
Source dataset: uspto-grants-1976_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03980666

Reaction notes

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