Acetic Acid → HCID 59497321, compound

HRID 1747433Notes

Reaction equation

HRID 1747433 reaction equation
C([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[CH3:30])[N:23]([CH3:31])[CH:22]=2)[C:12]1=[O:32])=[O:5])C.O.[OH-].[Li+].C(O)(=O)C>CO.O>[CH3:31][N:23]1[C:24]2[C:29](=[C:28]([CH3:30])[CH:27]=[CH:26][CH:25]=2)[C:21]([CH2:20][N:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:11]([C:7]3[CH2:8][CH2:9][CH2:10][C:6]=3[C:4]([OH:5])=[O:3])[C:12]2=[O:32])=[CH:22]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 59497349HCID 59497349, compound

Product 1

HCID 59497321HCID 59497321, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 120 mg (0.28 mmol) of 2-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclopent-1-enecarboxylic acid ethyl ester and 23 mg (0.56 mmol, 2.0 eq.) of lithium hydroxide monohydrate in 5 mL of methanol and 1 mL of water was stirred at room temperature for 2.5 days. Then the pH of the resulting mixture was adjusted to 3 with acetic acid and diluted with water. The precipitate was collected and washed with water. The isolated light pink solid was pumped overnight to give 94 mg (84%) of 2-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-cyclopent-1-enecarboxylic acid as a light pink solid.

Workup

  1. customThe precipitate was collected
  2. washwashed with water

Sources & evidence

ORD record
ord-f21c7814ab91455aa2d1cbb737fc46b5
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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