Lithium Hydroxide → HCID 71572173, compound

HRID 626407Notes

Reaction equation

HRID 626407 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]([C:15]2[CH:40]=[CH:39][C:18]3[N:19]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]5[C:30]([C:35]([O:37]C)=[O:36])=[N:31][CH:32]=[CH:33][CH:34]=5)=[CH:25][CH:24]=4)[CH:20]=[N:21][C:17]=3[CH:16]=2)=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[Li+].[OH-]>CO.O>[CH:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]([C:15]2[CH:40]=[CH:39][C:18]3[N:19]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([C:29]5[C:30]([C:35]([OH:37])=[O:36])=[N:31][CH:32]=[CH:33][CH:34]=5)=[CH:25][CH:24]=4)[CH:20]=[N:21][C:17]=3[CH:16]=2)=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 118072730HCID 118072730, compound

Product 1

HCID 71572173HCID 71572173, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (S)-methyl 3-(4-((5-(1-(3-isopropylphenyl)ethylcarbamoyl)-1H-benzo[d]imidazol-1-yl)methyl)phenyl)picolinate (30 mg, 0.056 mmol) in methanol (5 mL) and water (1 mL) was added LiOH (11 mg, 0.28 mmol), then the mixture was stirred at RT for 2 hrs. The methanol was removed under the reduced pressure. The residue in water was adjusted to pH=7 with 3N HCl, 1.5 then the mixture was concentrated. The residue was purified with prep-TLC (DCM/Methanol=10/1, silica gel) to get the titled compound.

Workup

  1. customThe methanol was removed under the reduced pressure
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified with prep-TLC (DCM/Methanol=10/1, silica gel)

Sources & evidence

ORD record
ord-ea8fe3213a4f4ea0a14030164296a82e
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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