Ethyl chloroacetate → HCID 86340127, compound

HRID 2276281Notes

Reaction equation

HRID 2276281 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]([CH:13]=[C:14]([Br:17])[C:15]=1[CH3:16])[NH2:12].C(=O)([O-])[O-].[Li+].[Li+]>CN1CCCC1=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH:12][C:11]1[CH:10]=[C:9]([Br:8])[C:15]([CH3:16])=[C:14]([Br:17])[CH:13]=1)[CH3:7]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11125Lithium CarbonateHCID 70157793,5-Dibromo-4-methylaniline

Product 1

HCID 86340127HCID 86340127, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The DNA ligase inhibitor L67 (10) was synthesized by incubation of ethyl chloroacetate with 3,5-dibromo-4-methylaniline in the presence of lithium carbonate in N-methyl-2-pyrrolidinone as the solvent at 100° C. for 16 hours to produce N-(3,5-dibromo-4-methylphenyl)glycine ethyl ester in 33% yield after recrystallization from ethanol.

Sources & evidence

ORD record
ord-116275f650ef4720818cc70fde8f0a2a
Source dataset
uspto-grants-2015_09
Patent number
US09132120B1

Reaction notes

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