Nitrous Acid → 2-Thiopheneacetic acid, alpha-amino-, (-)-
Reaction equation
C([NH:4][CH:5]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[C:6]([OH:8])=[O:7])(=O)N.N(O)=O>>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH:5]([C:6]([OH:8])=[O:7])[NH2:4]Participants
Procedure
Each thus obtained N-carbamoyl-2-(2-thienyl)glycine was subjected to decarbamoylation by reacting it with nitrous acid to give 2-(2-thienyl)glycine as follows: To a mixture of 5.0 g. of N-carbamoyl-D-(2-thienyl)glycine, 10 ml. of conc. HCl and a 100 ml. of a 50% aqueous acetic acid, 8.6 g. of a 20% aqueous solution of NaNO2 was added at 10° C. with stirring. After the completion of adding NaNO2, the reaction was carried out at 10° C. for 2 hours. The formed D-2-(2-thienyl)glycine was isolated by adsorption on an anion-exchange resin (commercially available under the registered trademark "Amberlite IR-120B" made by Rohm & Haas Co.) followed by elution with ammonia water. The fraction obtained was concentrated and neutralized with hydrochloric acid. D-2-(2-thienyl)glycine was collected and recrystallized from an aqueous ethanol. The amount of the obtained D-2-(2-thienyl)glycine was 2.9 g.
Sources & evidence
- ORD record
- ord-58551ede66ac411bba4f161c3ac0a3da
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04242452
Reaction notes
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