O-benzylglycine toluene-p-sulphonate → N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester

HRID 1646310ノート

反応式

HRID 1646310 の反応式
[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

参加物

5

反応物 2

HCID 6451311O-benzylglycine toluene-p-sulphonateHCID 8520682Cyanomethyl 3-(t-butyloxycarbonylamino)benzoate

生成物 1

HCID 15670374N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl ester収率 18.8%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-908df185f58e43fbb5636bddb6f6ae82
出典データセット
uspto-grants-1993_01
特許番号
US05179125

反応ノート

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