Lithium hydroxide, monohydrate → HCID 67538829, compound

HRID 1192372Notes

Reaction equation

HRID 1192372 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:27])[C:8]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)([F:19])[CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C>O.C1COCC1.CO>[C:15]([O:14][C:12]([NH:11][CH2:10][CH2:9][C:8]([C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)([F:19])[C:7]([OH:27])=[O:6])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67538549HCID 67538549, compound

Product 1

HCID 67538829HCID 67538829, compoundYield 74.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.27 g, 6.45 mmol) in H2O (5 mL) was added to a solution of 4-tert-butoxycarbonylamino-2-(4-chlorophenyl)-2-fluoro-butyric acid ethyl ester (580 mg, 1.61 mmol) in THF (5 mL) and MeOH (5 mL). After being stirred for 12 hours, the mixture was concentrated in vacuo, diluted with H2O, and extracted with DCM (3 times, discarded). The aqueous phase was then acidified to pH 1 and extracted with DCM (2 times). The organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give 4-tert-butoxycarbonylamino-2-(4-chlorophenyl)-2-fluoro-butyric acid (400 mg). The material was used in the following step without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with H2O
  3. extractionextracted with DCM (3 times, discarded)
  4. extractionextracted with DCM (2 times)
  5. dry with materialThe organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3d896d564444d3887259803abfb9ee2
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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