Lithium hydroxide, monohydrate → HCID 57520097, compound

HRID 83148Notes

Reaction equation

HRID 83148 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([NH:12][C:13]([C:15]2[CH:16]=[N:17][C:18]([O:21][CH2:22][C:23]3[C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:25][O:26][C:27]=3[CH3:28])=[CH:19][CH:20]=2)=[O:14])[CH2:7]1)C.O.[OH-].[Li+]>C1COCC1.O.CO.Cl>[CH3:28][C:27]1[O:26][N:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]=1[CH2:22][O:21][C:18]1[N:17]=[CH:16][C:15]([C:13]([NH:12][CH:8]2[CH2:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:35])=[O:3])[CH2:7]2)=[O:14])=[CH:20][CH:19]=1

Participants

8

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68445346(3-{[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acid ethyl ester

Product 1

HCID 57520097HCID 57520097, compoundYield 84.8%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 887MethanolCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-{[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acid ethyl ester (538 mg, 1.1 mmol) in THF (5 mL) was added a solution of lithium hydroxide monohydrate (94 mg, 2.2 mmol) in water (5 mL) and methanol (1 mL) added and the resulting mixture stirred at room temperature overnight. The mixture was acidified to pH 4 with HCl (25%, 3 drops) and methanol (2 drops) added. A gum began to form and the mixture was cooled at 0° C. for 1.5 h and then the aqueous layer decanted off. Trituration with diethylether and hexane afforded the title compound (420 mg, 83%) which was obtained as an off white solid. MS: m/e=449.0 [M−H].

Workup

  1. additionadded
  2. additionadded
  3. customto form
  4. temperaturethe mixture was cooled at 0° C. for 1.5 h
  5. customthe aqueous layer decanted off

Sources & evidence

ORD record
ord-bf94ae6552c74d1c82924aaa06d172c4
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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