Hydrochloric Acid → Methyl 2-amino-3-(phenylsulfanyl)propanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([N:13]=[N+]=[N-])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[H][H]>CO.[Re]>[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH2:13])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
Procedure
0.91 gram (3.84 mmoles) of the 2-azido-3-phenylmercapto-propionic acid methyl ester obtained in Example 2 in 8 ml of methanol was treated with 0.28 gram (7.68 mmoles) of hydrogen chloride, 1 mole % of rhenium VII sulfide based on the azido compound employed was added and the mixture hydrogenated in an autoclave at a hydrogen pressure of 60 bar at 25° C. for 3.5 hours. After the end of the reaction the catalyst was filtered off with suction, the solvent remained under reduced pressure and the residue treated with 20 ml of acetone. After addition of 20 ml of diethyl ether for complete precipitation, the precipitate was filtered off with suction, then washed with diethyl ether and dried at 40° C. for 12 hours under reduced pressure. There were obtained 0.65 gram (68% of theory) of 2-amino-3-phenylmercapto-propionic acid methyl ester.HCl with a melting point of 123° to 125° C.
Workup
- additionemployed was added
- customAfter the end of the reaction the catalyst
- filtrationwas filtered off with suction
- additionthe residue treated with 20 ml of acetone
- additionAfter addition of 20 ml of diethyl ether
- customfor complete precipitation
- filtrationthe precipitate was filtered off with suction
- washwashed with diethyl ether
- customdried at 40° C. for 12 hours under reduced pressure
Sources & evidence
- ORD record
- ord-fa846467bfa343a590d7b51f65cd936e
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04523012
Reaction notes
Loading…