Hydrochloric Acid → HCID 14763101, compound

HRID 1646353Notes

Reaction equation

HRID 1646353 reaction equation
[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[CH:16][N:15]([CH2:18][C:19]4[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][C:20]=4[O:29][CH3:30])[C:14]=3[CH:31]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[CH:16][N:15]([CH2:18][C:19]4[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=4[O:29][CH3:30])[C:14]=3[CH:31]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 14763099Methyl 4-[6-(cyclopentyloxycarbonyl)aminobenzimidazol-1-ylmethyl]-3-methoxybenzoate

Product 1

HCID 14763101HCID 14763101, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of methyl 4-[6-(cyclopentyloxycarbonyl)aminobenzimidazol-1-ylmethyl]-3methoxybenzoate in 1:1 v/v tetrahydrofuran:methanol (7 ml.) was treated with water (1.4 ml.) and lithium hydroxide monohydrate (0.3 g.). Stirring was continued at ambient temperature for 4 hours. The solvent was then evaporated. The resultant residue was dissolved in water. The solution obtained was acidified with 10% v/v hydrochloric acid. The resultant precipitate was collected by filtration to give the title compound (0.43 g., 78%). An analytical sample was obtained as a white powder by recrystallization from aqueous ethanol; m.p. 241°-242° C.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionThe resultant residue was dissolved in water
  3. customThe solution obtained
  4. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-542f9fc4517b436482a7ba93fb6405e6
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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