Hydrochloric Acid → (2r,3s)-3-Phenylisoserine amide hydrochloride
Reaction equation
C(C(C(O)=O)(O)C(C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[C:27]1([C@@H:33]([C@H:35]([C:37]([NH2:39])=[O:38])[OH:36])[NH2:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[ClH:40]>C(O)C>[ClH:40].[C:27]1([C@@H:33]([C@H:35]([C:37]([NH2:39])=[O:38])[OH:36])[NH2:34])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 42 °C
Procedure
(2R,3S)-3-Phenylisoserine amide dibenzoyl-tartaric acid salt (X) (180.6 g, 0.34 mole) was suspended in ethanol (535.0 g) and the mixture was heated to 42° C. 46.2 g of concentrated hydrochlorid acid (32%) was then slowly added to the suspension keeping the temperature at about 45° C. After completion of the addition the mixture was cooled down to 0° C. over a period of 1 hour and stirred for 1 further hour. The product was filtered off, washed with ethanol (100.0 g) and vacuum dried at 80° C. Yield: 60.5 g (0.28 mole, 82.0%).
Workup
- customat about 45° C
- additionAfter completion of the addition the mixture
- temperaturewas cooled down to 0° C. over a period of 1 hour
- filtrationThe product was filtered off
- washwashed with ethanol (100.0 g) and vacuum
- customdried at 80° C
Sources & evidence
- ORD record
- ord-c6993698eaa14a10bde22bef4070bc11
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106231B2
Reaction notes
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