Acetonitrile → Rac.-2-amino-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester p-toluenesulfonic acid salt

HRID 487805Notes

Reaction equation

HRID 487805 reaction equation
[CH2:1]([O:8][C:9](=[O:39])[CH:10]([N:25]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1.C(#N)C>O>[C:41]1([CH3:51])[CH:42]=[CH:43][C:44]([S:47]([OH:50])(=[O:48])=[O:49])=[CH:45][CH:46]=1.[CH2:1]([O:8][C:9](=[O:39])[CH:10]([NH2:25])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 14888672Rac.-2-((diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy) carbonyl]phenyl]propanoic acid benzyl ester

Product 1

HCID 86746526Rac.-2-amino-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester p-toluenesulfonic acid saltYield 68.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of rac.-2-[(diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester (11.5 g. 22 mmol) and p-toluenesulfonic acid monohydrate (4.18 g. 22 mmol) in a 10/1 mixture of acetonitrile and water (640 ml) was stirred for 2 h at room temperature. Concentration provided a crude solid product which was recrystallized from ethanol-ether to give rac.-2-amino-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester p-toluenesulfonic acid salt, (8.1 g, 15 mmol) in 67% yield. mp. 154°-157° C. Following the previous procedure, the analogs listed below were prepared.

Workup

  1. concentrationConcentration
  2. customprovided a crude solid product which
  3. customwas recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-229c3d3488804a2ba177f45a104f35e5
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

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