Potassium Carbonate → t-Butyl 4-benzyloxycarbonylaminophenoxyacetate

HRID 1900877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900877
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([O:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([O:17][C:18]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[CH:25][CH:26]=1)=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 293061Benzyl (4-hydroxyphenyl)carbamate

Produkt 1

HCID 23370045t-Butyl 4-benzyloxycarbonylaminophenoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

t-Butyl bromoacetate (15.5 ml) was added dropwise over 10 minutes to a mixture of the product of step (a) (21 g), anhydrous potassium carbonate (20 g) and acetone (450 ml). On completion of the addition the reaction mixture was stirred at ambient temperature overnight. Insoluble material was removed by filtration and the filtrate was evaporated to dryness. The solid residue was crystallised from ethyl acetate to give t-butyl 4-benzyloxycarbonylaminophenoxyacetate (25.1 g) as a white solid: m.p. 109°-110° C.; NMR Spectrum (DMSO-d6) 1.42 (9H, s), 4.56 (2H, s), 5.12 (2H, s), 6.82 (2H, d), 7.31-7.43 (7H, m), 9.54 (1H, br s).

Aufarbeitung

  1. additionOn completion of the addition the reaction mixture
  2. customInsoluble material was removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customThe solid residue was crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1b6fd3ef9ef040fb8fe66a12c8713e04
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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