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

HRID 248703노트

반응식

HRID 248703 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8471Triethylamine용매

반응 조건

온도
80 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-29cbf6febb084778a63f0059026df00a
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210266

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