Hydrochloric Acid → HCID 178490883, compound

HRID 1370142Notes

Reaction equation

HRID 1370142 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=3[N:10]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([O:30]C)=[O:29])[CH:21]=3)[C:9]2=[O:32])[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CO.O1CCCC1>[C:28]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[CH2:19][N:10]1[C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][C:12]=2[N:8]([C@H:5]2[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]2)[C:9]1=[O:32])([OH:30])=[O:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178498106HCID 178498106, compound

Product 1

HCID 178490883HCID 178490883, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
600 °C

Procedure

To a solution of 1-(trans-4-hydroxycyclohexyl)-3-(4-methoxy-3-methoxycarbonylbenzyl)-5-cyano-2,3-dihydro-1H-benzimidazole-2-one (120 mg) in methanol (10 mL) and tetrahydrofuran (2 mL) was added 1N-aqueous sodium hydroxide solution (3 mL) and the mixture was stirred at 600° C. for an hour. After the solution was acidified with 1N-hydrochloric acid, the organic solvent of the solution was removed by evaporation. The aqueous layer was diluted with water and extracted with a mixture of chloroform and methanol (4:1). The separated organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 3-(3-carboxy-4-methoxybenzyl)-1-(trans-4-hydroxycyclohexyl)-5-cyano-2,3-dihydro-1H-benzimidazole-2-one as a colorless powder (88.8 mg).

Workup

  1. customthe organic solvent of the solution was removed by evaporation
  2. additionThe aqueous layer was diluted with water
  3. extractionextracted with a mixture of chloroform and methanol (4:1)
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-66365d99cdf94fa8af0c62841243920f
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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