Lithium hydroxide, monohydrate → HCID 59497480, compound

HRID 1747359Notes

Reaction equation

HRID 1747359 reaction equation
C[O:2][C:3](=[O:30])[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][C:19]([Cl:28])=[C:20]3[C:24]=2[N:23]([CH3:25])[C:22]([CH3:26])=[C:21]3[CH3:27])[C:7]1=[O:29].O.[OH-].[Li+]>C1COCC1.O>[Cl:28][C:19]1[CH:18]=[CH:17][C:16]([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:30])=[O:2])[C:7]2=[O:29])=[C:24]2[C:20]=1[C:21]([CH3:27])=[C:22]([CH3:26])[N:23]2[CH3:25]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59497316HCID 59497316, compound

Product 1

HCID 59497480HCID 59497480, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[3-(4-chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester (40 mg, 0.09 mmol) in THF (3 ml) and water (1 ml) was added lithium hydroxide monohydrate (10 mg, 0.24 mmol). The resulting mixture was stirred at ambient temperature until all of the starting material was consumed. After this time the reaction was concentrated to low volume and diluted with water (10 ml) and acetic acid (0.5 ml). The resulting heterogeneous mixture was stirred at ambient temperature for 18 h. The solid product was collected via filtration and suspended in acetonitrile. The product was collected once more via filtration and washed with minimal acetonitrile to give 5 mg (13%) of the desired product. LCMS (ESMS): m/z 412.88 (M+H+).

Workup

  1. customwas consumed
  2. concentrationAfter this time the reaction was concentrated to low volume
  3. additiondiluted with water (10 ml) and acetic acid (0.5 ml)
  4. stirringThe resulting heterogeneous mixture was stirred at ambient temperature for 18 h
  5. filtrationThe solid product was collected via filtration
  6. filtrationThe product was collected once more via filtration
  7. washwashed with minimal acetonitrile

Sources & evidence

ORD record
ord-74a57ac6ccda432f998b247d0cdf4780
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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