Potassium Carbonate → t-Butyl 4-benzyloxycarbonylaminophenoxyacetate

HRID 1900877Notes

Reaction equation

HRID 1900877 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 23370045t-Butyl 4-benzyloxycarbonylaminophenoxyacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1b6fd3ef9ef040fb8fe66a12c8713e04
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

Loading…