Triethylamine → HCID 20083705, compound

HRID 1609019Notes

Reaction equation

HRID 1609019 reaction equation
C(N(CC)CC)C.ClC(O[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[CH3:19][O:20][C:21](=[O:43])[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][C:33](=[O:42])[C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[CH3:19][O:20][C:21](=[O:43])[CH2:22][N:23]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][NH:32][C:33](=[O:42])[C:34]2[CH:35]=[CH:36][C:37]([C:40]#[N:41])=[CH:38][CH:39]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 20083620HCID 20083620, compound

Product 1

HCID 20083705HCID 20083705, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

1.2 ml of triethylamine and 3 ml of benzyl chloroformate (50% in toluene) were added to a solution of 675 mg of N-[p-[2-(p-cyanobenzamido)ethyl]phenyl]glycine methyl ester in 15 ml of chloroform. The reaction mixture was maintained at 50° C. overnight. After working up and chromatography on silica gel with ether/petroleum ether 2:1, 500 mg of crystalline N-benzyl-N-[p-[2-(p-cyanobenzamido)ethyl]phenyl]glycine methyl ester, melting point 123°-124° C., were isolated.

Sources & evidence

ORD record
ord-a9f3ce3f7efb4e44966a2a60a5de2b27
Source dataset
uspto-grants-1995_03
Patent number
US05399585

Reaction notes

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