Butyl chloroformate → Methyl 4-[6-(butoxycarbonyl)aminobenzimidazol-1-ylmethyl]-3-methoxybenzoate

HRID 275141Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=3[O:29][CH3:30])[C:14]=2[CH:31]=1>>[CH2:5]([O:4][C:2]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=3[O:29][CH3:30])[C:14]=2[CH:31]=1)=[O:3])[CH2:6][CH2:7][CH3:8]

Participants

Reactant 2

HCID 61140Butyl chloroformate

HCID 14763098Methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365847Methyl 4-[6-(butoxycarbonyl)aminobenzimidazol-1-ylmethyl]-3-methoxybenzoateYield 34%

Procedure

Using a similar procedure to that described in Example 35, but using butyl chloroformate and (J), the title compound was obtained as a solid in 34% yield; partial NMR: 0.9(t,3H, CH3CH2), 1.4(m,2H, CH3CH2), 1.6(m,2H, CH2CH2O), 4.1(t,2H, CH2O).

Sources & evidence

ORD record: ord-600ba59279c74ecab94b3bf66afa1e51
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05391758

Reaction notes

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