Benzene → HCID 54316730, compound

HRID 648253Notes

Reaction equation

HRID 648253 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-48cdfd2a37744e1785c55f8a55722bc8
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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