Lithium hydroxide, monohydrate → HCID 69292797, compound

HRID 1247393Notes

Reaction equation

HRID 1247393 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH:11]([C:14](=[O:25])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[O:12][CH3:13])[C:5]=1[F:26].O[Li].O>C1COCC1.CO.O>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:14]([CH:11]([O:12][CH3:13])[C:6]2[C:5]([F:26])=[C:4]([CH:9]=[CH:8][C:7]=2[F:10])[C:3]([OH:27])=[O:2])=[O:25])=[CH:18][CH:19]=1)#[N:24]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69289078HCID 69289078, compound

Product 1

HCID 69292797HCID 69292797, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of (RS)-3-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-2,4-difluoro-benzoic acid methyl ester (2.05 g) and LiOH.H2O (241 mg) in THF/MeOH/H2O 1:1:0.5 (75 ml) was stirred 1 h at rt. The organic solvents were evaporated, ice cold H2O (50 ml) was added and the pH was lowered (pH=2) by addition of 2 N aq. HCl sol. The product was extracted with AcOEt (2×120 ml). The organic layers were washed with brine (100 ml), combined and dried over Na2SO4. Evaporation of the solvent yielded 1.80 g of (RS)-3-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-2,4-difluoro-benzoic acid. White solid. MS 359.4 ([M−H]).

Workup

  1. customThe organic solvents were evaporated
  2. additionice cold H2O (50 ml) was added
  3. additionby addition of 2 N aq. HCl sol. The product
  4. extractionwas extracted with AcOEt (2×120 ml)
  5. washThe organic layers were washed with brine (100 ml)
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2c22aebc1cf942a6af781fa158d4aea7
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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