Acetic Acid → 2-Amino-2-(4-carboxy-2-[(2-phenylethyl)thio]phenyl)acetic acid
Reaction equation
C(C1[CH:8]=[CH:7][C:6]([CH:9]2[NH:13]C(=O)N[C:10]2=[O:15])=[C:5]([S:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:4]=1)#N.[OH-:25].[Na+].Cl.[C:28]([OH:31])(=[O:30])[CH3:29]>>[NH2:13][CH:9]([C:6]1[CH:7]=[CH:8][C:29]([C:28]([OH:31])=[O:30])=[CH:4][C:5]=1[S:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:10]([OH:15])=[O:25]Participants
5
Procedure
A stirred solution of 5-(4-cyano-2-(2-phenylethylthio)phenyl)hydantoin (1.20 g, 3.56 mmol) in 2M sodium hydroxide (10 ml, 20 mmol) was heated under reflux for 72 hours. The cooled solution was acidified with 5M hydrochloric acid (2 ml, 20 mmol), then with acetic acid (1 ml) to pH~4. The pale solid was filtered (0.9 g), washed with CHCl3 (10 ml) and redissolved in water (10 ml) and 0.880 ammonia solution (0.1 ml). The solution was acidified with acetic acid (0.4 ml) to precipitate a fine solid that was filtered and washed with methanol to give the title product as an off-white solid, m.p. 227°-231° C.
Workup
- temperatureunder reflux for 72 hours
- filtrationThe pale solid was filtered (0.9 g)
- washwashed with CHCl3 (10 ml)
- dissolutionredissolved in water (10 ml)
- customto precipitate a fine solid
- filtrationthat was filtered
- washwashed with methanol
Sources & evidence
- ORD record
- ord-3d492523781746a19b5e8676c1f09e2d
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05863947
Reaction notes
Loading…