Potassium Carbonate → HCID 19389039, compound

HRID 1757858Notes

Reaction equation

HRID 1757858 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:33]1([CH2:32][O:31][C:29](=[O:30])[CH2:28][NH:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 4457732HCID 4457732, compound

Product 1

HCID 19389039HCID 19389039, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.08 g (3.0 mmol) of 3-(octadecyloxy)benzenamine, 0.52 ml (3.3mmol) of benzyl bromoacetate and 0.8 g (6.0 mmol) of potassium carbonate in40 ml of acetone was stirred at reflux under argon for 18 hours. The reaction mixture was filtered and the filtrate was concentrated at reducedpressure to an oil which was purified by chromatography on 150 g of silica gel using 20% ethyl acetate-hexane to give 1.1 g (72% yield, mp 55°-60°) of N-[3-(octadecyloxy) phenyl]glycine phenylmethyl ester.

Workup

  1. temperatureat reflux under argon for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reducedpressure to an oil which
  4. customwas purified by chromatography on 150 g of silica gel using 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-f274a006bb3c45528cca83f5c7901d0e
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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