Ammonia → DL-cysteine
Reaction equation
[CH2:1]1[S:5][CH2:4][NH:3][CH:2]1[C:6]([OH:8])=[O:7].[Na].N.[CH2:11]1[S:15][CH2:14][NH:13][C@H:12]1[C:16]([OH:18])=[O:17]>>[C:6]([CH:2]([NH:3][CH2:4][CH2:14][NH:13][CH:12]([C:16]([OH:18])=[O:17])[CH2:11][SH:15])[CH2:1][SH:5])([OH:8])=[O:7].[NH2:3][CH:2]([C:6]([OH:8])=[O:7])[CH2:1][SH:5].[CH2:6]=[O:7]Participants
7
Procedure
The L,L-isomer of the title compound is prepared by reductive dimerisation of L-thiazolidine-4-carboxylic acid under the influence of sodium in liquid ammonia, as described in Blondeau et al in Can. J. Chem. 45 (1), 49-52 (1967). The corresponding D,D-isomer and the meso form (L,L-isomer) are prepared in a corresponding manner from D-thiazolidine-4-carboxylic acid and racemic thiazolidine-4-carboxylic acid, respectively. These thiazolidine carboxylic acids are obtained by reaction of L-, D- or DL-cystein with formaldehyde according to Nagasama et al, J. Med. Chem. 27, 591 (1984).
Sources & evidence
- ORD record
- ord-c032a8e4059e496d9ac986e8316051f1
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04925650
Reaction notes
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