Lithium Hydroxide → HCID 59515433, compound

HRID 1160254Notes

Reaction equation

HRID 1160254 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][C@@H:19]3[CH2:23][CH2:22][N:21]([CH:24]4[CH2:29][CH2:28][C:27]([F:31])([F:30])[CH2:26][CH2:25]4)[C:20]3=[O:32])=[C:13]([Cl:33])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[Cl:33][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH:16]=[C:15]([Cl:17])[C:14]=1[CH2:18][C@@H:19]1[CH2:23][CH2:22][N:21]([CH:24]2[CH2:25][CH2:26][C:27]([F:31])([F:30])[CH2:28][CH2:29]2)[C:20]1=[O:32]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59515432HCID 59515432, compound

Product 1

HCID 59515433HCID 59515433, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Treat a solution of 3′,5′-Dichloro-4′-[(R)-1-(4,4-difluoro-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (Preparation 14) (1.0 g, 2.0 mmol) in THF/water (15 mL/5 mL) with 2M aqueous LiOH (3.0 mL). Stir the reaction overnight at room temperature. Quench the reaction with 1N HCl and extract with EtOAc. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 0.97 g (100%) of desired product. MS (m/e): 482 (M+1).

Workup

  1. customthe reaction overnight at room temperature
  2. customQuench
  3. customthe reaction with 1N HCl
  4. extractionextract with EtOAc
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-5a712216f9a64033bc4a32e017e77458
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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