N-(tert-butoxycarbonyl)glycine → N-(2-Benzyloxyphenyl)-2-(N-tertiary butoxycarbonylamino)acetamide

HRID 581180

Reaktionsgleichung

Reaktionsgleichung von HRID 581180
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH:11][C:25](=[O:26])[CH2:24][NH:23][C:21]([O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 2405482-BenzyloxyanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 10760721N-(2-Benzyloxyphenyl)-2-(N-tertiary butoxycarbonylamino)acetamideAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Benzyloxyaniline (S1) (16.4 g), 4-dimethylamino-pyridine (11.0 g), and N-tertiarybutoxycarbonylglycine (14.4 g) were dissolved in dichloromethane. To the resulting solution, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (16.3 g) was added and stirred for 12 hours at room temperature. The reaction mixture was washed -successively with 1N HCl, saturated aqueous sodium hydrogencarbonate solution and brine, then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, obtaining 11.5 g of the compound S2 as white powder.

Aufarbeitung

  1. washThe reaction mixture was washed -successively with 1N HCl, saturated aqueous sodium hydrogencarbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b44b8e5944b745e288b15e69b0db9131
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919824

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