Triethylamine → N-(p-Chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester

HRID 464006Notes

Reaction equation

HRID 464006 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][O:19][C:20](=[O:45])[C@:21]([CH2:41][CH2:42][C:43]#[N:44])([CH3:40])[NH:22][C:23](=[O:39])[C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>ClCCl>[CH3:18][O:19][C:20](=[O:45])[C@:21]([CH2:41][CH2:42][C:43]#[N:44])([CH3:40])[NH:22][C:23](=[O:39])[C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30].[CH3:18][O:19][C:20](=[O:45])[C@:21]([CH2:41][CH2:42][C:43]#[N:44])([CH3:40])[NH:22][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 54540171N-(N-benzyloxycarbonyl-L-prolyl)-2-(2-cyanoethyl)alanine methyl ester

Product 2

HCID 53771201N-(p-Chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl esterHCID 54540171N-(N-benzyloxycarbonyl-L-prolyl)-2-(2-cyanoethyl)alanine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Chlorobenzoyl chloride (0.91 g) and triethylamine (0.91 ml) were added at 5° C. to a solution of 0.85 g of isomer (i) of the 2-(2-cyanoethyl)alanine methyl ester in dichloromethane (20 ml), and the resulting mixture was stirred at 0°-5° C. for 2 hours. The reaction mixture was then washed with water (20 ml) and the organic layer was dried over magnesium sulphate. The solvent was distilled off and the residue was purified by silica gel Lobar column chromatography (eluent: 1/1 cyclohexane/ethyl acetate; flow rate: 12 ml/minute), giving 1.13 g of isomer (i) of the desired product as a colourless powder.

Workup

  1. washThe reaction mixture was then washed with water (20 ml)
  2. dry with materialthe organic layer was dried over magnesium sulphate
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by silica gel Lobar column chromatography (eluent: 1/1 cyclohexane/ethyl acetate; flow rate: 12 ml/minute)

Sources & evidence

ORD record
ord-6f44b58168394d25b36cbdea420b052c
Source dataset
uspto-grants-1985_10
Patent number
US04545942

Reaction notes

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