Benzene → HCID 54316730, compound

HRID 1389348Notes

Reaction equation

HRID 1389348 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C@H:18]([C:22]([OH:24])=[O:23])[CH:19]([CH3:21])[CH3:20])=[CH:13][CH:12]=1.C1C=CC=CC=1>O.CCOCC>[Cl:1][C:15]1[CH:16]=[C:11]([O:10][CH3:9])[CH:12]=[CH:13][C:14]=1[NH:17][C@H:18]([C:22]([OH:24])=[O:23])[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 241BenzeneHCID 31398ChlorosuccinimideHCID 54496950HCID 54496950, compound

Product 1

HCID 54316730HCID 54316730, compound

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

A mixture of N-chlorosuccinimide (1.17 mmole), m-phenoxybenzyl ester of N-(p-methoxyphenyl)valine (1.23 mmole) and benzene (20 ml) is refluxed under nitrogen for about 60 hours. The reaction is worked up in water/ether. The ether layer is washed with water and brine and dried over sodium sulfate. The crude product is purified by preparatory TLC eluting with 15% ether/hexane to give the m-phenoxybenzyl ester of N-(2-chloro-4-methoxyphenyl)valine, MS m/e 439 (M+, 7.4), 212 (100).

Workup

  1. temperatureis refluxed under nitrogen for about 60 hours
  2. washThe ether layer is washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe crude product is purified by preparatory TLC
  5. washeluting with 15% ether/hexane

Sources & evidence

ORD record
ord-d6b0f7f1d70c4c97b48c092caf794add
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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