Penicillamine → (3S)-2,2-Dimethyl-1,4-thiazinane-3-carboxylic acid
Reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[CH2:10]1CCN2C(=NCCC2)C[CH2:11]1.C[Si](Cl)(C)C>ClC(Cl)C.CN(C=O)C>[CH3:4][C:3]1([CH3:5])[S:6][CH2:11][CH2:10][NH:1][C@H:2]1[C:7]([OH:9])=[O:8]Participants
6
Procedure
To a 0° suspension of 14.92 g (0.10 mmol) of D-penicillamine in 300 mL of dichloroethane and 2.0 mL of DMF was added 22.4 mL of DBU followed by 19.0 mL of trimethylsilyl chloride. The ice bath was removed and the reaction was stirred for 3 h, after which an additional 29.9 mL of DBU was added. The reaction was stirred overnight at room temperature and then 10 mL of methanol was added and the reaction was stirred for 1 h. The resulting white precipitate was filtered off, washed with 10 mL of methanol and dried in vacuo to provide 16 g of (3S)-2,2-dimethyl-3-thiomorpholine carboxylic acid as a white solid.
Workup
- customThe ice bath was removed
- additionafter which an additional 29.9 mL of DBU was added
- stirringThe reaction was stirred overnight at room temperature
- addition10 mL of methanol was added
- stirringthe reaction was stirred for 1 h
- filtrationThe resulting white precipitate was filtered off
- washwashed with 10 mL of methanol
- customdried in vacuo
Sources & evidence
- ORD record
- ord-d80bf00864e444e585087db425ebfa88
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06716833B2
Reaction notes
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