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

HRID 1646310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646310
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 15670374N-[3-(t butyloxycarbonylamino)benzoyl]glycine benzyl esterAusbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-908df185f58e43fbb5636bddb6f6ae82
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05179125

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