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

HRID 248703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248703
[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

6

Edukt 3

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

Produkt 1

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

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). m.p.: 171°-173° C. (colorless needles) IR (KBr; cm-1): 1725, 1695, 1640

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-29cbf6febb084778a63f0059026df00a
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210266

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