Hydrochloric Acid → 1-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-2-ethyl-1H-benzimidazole

HRID 2287572Notes

Reaction equation

HRID 2287572 reaction equation
[Cl:1][C:2]1[C:26]([N:27]([CH3:46])[C:28](=[O:45])[CH2:29][NH:30][C:31](=[O:44])[CH:32]=[CH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40](=[O:43])[NH:41][CH3:42])=[CH:36][CH:35]=2)=[CH:25][CH:24]=[C:23]([Cl:47])[C:3]=1[CH2:4][O:5][C:6]1[C:14]2[N:13]=[C:12]([CH2:15][CH3:16])[N:11]([CH2:17][C:18]([O:20]CC)=[O:19])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[C:18]([CH2:17][N:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([O:5][CH2:4][C:3]3[C:23]([Cl:47])=[CH:24][CH:25]=[C:26]([N:27]([CH3:46])[C:28](=[O:45])[CH2:29][NH:30][C:31](=[O:44])[CH:32]=[CH:33][C:34]4[CH:35]=[CH:36][C:37]([C:40](=[O:43])[NH:41][CH3:42])=[CH:38][CH:39]=4)[C:2]=3[Cl:1])[C:14]=2[N:13]=[C:12]1[CH2:15][CH3:16])([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 536707184-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole

Product 1

HCID 542002691-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-2-ethyl-1H-benzimidazoleYield 108.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole (270 mg) in ethanol (3 ml) was added 1N sodium hydroxide solution (0.44 ml), and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was acidified with 1N hydrochloric acid, and the solvent was removed in vacuo. The residue was pulverized with 99% acetonitrile to give 1-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-2-ethyl-1H-benzimidazole (280 mg) as pale yellow solid.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-084706462d384a39bb13a1b8dfd19e12
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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