Ethyl chloroacetate → 1-(ethoxycarbonylmethyl)-2-chlorobenzimidazole

HRID 271539Notes

Reaction equation

[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH2:22]([O:21][C:19]([CH2:18][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[Cl:1])=[O:20])[CH3:23]

Participants

Reactant 3

HCID 7751Ethyl chloroacetate

HCID 11430Potassium Carbonate

HCID 785722-Chlorobenzimidazole

Product 1

HCID 41591541-(ethoxycarbonylmethyl)-2-chlorobenzimidazole

Procedure

2-Chlorobenzimidazole was treated with potassium carbonate and ethyl chloroacetate to yield 1-(ethoxycarbonylmethyl)-2-chlorobenzimidazole. This compound (1 eq.) was combined with L-4-(N,N-dimethylcarbamyloxy)phenylalanine tert-butyl ester (1.1 eq., prepared as described in Method L) and 2 drops of acetonitrile in a sealed tube and the reaction was heated for two days at 120° C. and the resultant mixture purified by column chromatography (1:3 ethyl acetate/hexanes) to yield the title compound.

Sources & evidence

ORD record: ord-8e1e77215bb147efb598897b27f76dde
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452912B2

Reaction notes

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