Lithium hydroxide, monohydrate → HCID 60026665, compound

HRID 400676Notes

Reaction equation

HRID 400676 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]2[CH:11]=[C:12]([CH2:14][C:15]([OH:34])([C:30]([F:33])([F:32])[F:31])[CH2:16][C:17]([C:20]3[C:28]4[O:27][CH2:26][CH2:25][C:24]=4[CH:23]=[C:22]([Cl:29])[CH:21]=3)([CH3:19])[CH3:18])[NH:13][C:8]2=[CH:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.CO.O.O.Cl>[Cl:29][C:22]1[CH:21]=[C:20]([C:17]([CH3:19])([CH3:18])[CH2:16][C:15]([OH:34])([C:30]([F:33])([F:31])[F:32])[CH2:14][C:12]2[NH:13][C:8]3[C:9](=[N:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=3)[CH:11]=2)[C:28]2[O:27][CH2:26][CH2:25][C:24]=2[CH:23]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 60026440HCID 60026440, compound

Product 1

HCID 60026665HCID 60026665, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

2-[4-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid methyl ester (100 mg, 0.2 mmol) was dissolved in 2 mL of THF-MeOH-water (3:1:1). Lithium hydroxide monohydrate (25 mg, 0.6 mmol) was added. The reaction was stirred at room temperature for 4 hours. The mixture was diluted with 5 mL of water and 6 N HCl solution was used to adjust the pH to about 2. The organic was extracted with three 50 mL portions of ethyl acetate, washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give the title compound (13.5 mg, 14% yield).

Workup

  1. extractionThe organic was extracted with three 50 mL portions of ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-18ee3f3c5b234fb88453fdb9358ded6c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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