p-Toluenesulfonic acid → N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester

HRID 248703Notes

Reaction equation

HRID 248703 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[C:12]([O:14]CC#N)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:21]([O:28][C:29](=[O:32])[CH2:30][NH:31][C:12](=[O:14])[C:11]1[CH:18]=[CH:19][CH:20]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:10]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 409140Benzyl glycinateHCID 8520682Cyanomethyl 3-(t-butyloxycarbonylamino)benzoate

Product 1

HCID 15670374N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Cyanomethyl 3-(t-butyloxycarbonylamino)-benzoate [compound of Example 61-(2)] (27.6 g), glycine benzyl ester.p-toluenesulfonate (33.7 g), triethylamine (20.2 g) and 4-dimethylaminopyridine (0.2 g) are mixed. The mixture is stirred at 80° C. two nights. The reaction mixture is extracted with ethyl acetate (200 ml). The extract is washed with water, and ethyl acetate is distilled off under reduced pressure. The residue is purified by a silica gel column chromatography (eluant, chloroform-ethyl acetate). The fractions containing the desired compound are collected, and the solvent is distilled off under reduced pressure. The residue is recrystallized from 70% aqueous acetonitrile to give N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester (7.2 g). m.p.: 171°-173° C. (colorless needles) IR (KBr; cm-1): 1725, 1695, 1640

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate (200 ml)
  2. washThe extract is washed with water, and ethyl acetate
  3. distillationis distilled off under reduced pressure
  4. customThe residue is purified by a silica gel column chromatography (eluant, chloroform-ethyl acetate)
  5. additionThe fractions containing the desired compound
  6. customare collected
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue is recrystallized from 70% aqueous acetonitrile

Sources & evidence

ORD record
ord-29cbf6febb084778a63f0059026df00a
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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