Lithium hydroxide, monohydrate → HCID 56670144, compound

HRID 1747384Notes

Reaction equation

HRID 1747384 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:24]=2[N:23]([CH3:25])[C:22]([CH3:26])=[CH:21]3)[C:7]1=[O:27].O.[OH-].[Li+]>C1COCC1.O>[CH3:25][N:23]1[C:24]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]([CH2:5][CH2:4][C:3]([OH:28])=[O:2])[C:7]2=[O:27])[CH:21]=[C:22]1[CH3:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59497590HCID 59497590, compound

Product 1

HCID 56670144HCID 56670144, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[3-(1,2-dimethyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester (90 mg, 0.24 mmol) in THF (3 ml) and water (0.5 ml) was added lithium hydroxide monohydrate (15 mg, 0.36 mmol). The reaction was stirred for 0.5 h and concentrated to low volume. The remaining residue was diluted with water and acetic acid (0.3 ml). The resulting suspension was stirred at ambient temperature over night. The precipitate was collected via filtration, washed with water and then suspended in 1:1 acetonitrile/water. The solid precipitate was isolated via filtration and dried to give 65 mg (87%) of 3-[3-(1,2-dimethyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid. LCMS (ESMS): m/z 364.41 (M+H).

Workup

  1. concentrationconcentrated to low volume
  2. additionThe remaining residue was diluted with water and acetic acid (0.3 ml)
  3. stirringThe resulting suspension was stirred at ambient temperature over night
  4. filtrationThe precipitate was collected via filtration
  5. washwashed with water
  6. customThe solid precipitate was isolated via filtration
  7. customdried

Sources & evidence

ORD record
ord-eee7f539ed184527be5ca86d06c9aff7
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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