Lithium hydroxide, monohydrate → HCID 67297078, compound

HRID 1807124Notes

Reaction equation

HRID 1807124 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=3[F:25])[C@:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[F:35])([C:26]#[N:27])[C@H:15]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[NH:14]2)=[O:12])[CH2:7][CH2:6]1.O[Li].O>CO.O>[ClH:24].[Cl:24][C:20]1[C:19]([F:25])=[C:18]([C@@H:17]2[C@:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[F:35])([C:26]#[N:27])[C@H:15]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[NH:14][C@H:13]2[C:11]([N:8]2[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:41])=[O:2])[CH2:10][CH2:9]2)=[O:12])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59249477HCID 59249477, compound

Product 1

HCID 67297078HCID 67297078, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of rac {1-[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-piperidin-4-yl}-acetic acid methyl ester (556 mg, 0.92 mmol) in methanol (8 mL), LiOH.H2O (Aldrich, 80 mg) in 1 mL of water was added. The mixture was stirred at 60° C. overnight. The reaction was quenched with addition of water. The mixture was filtered and the filtrate was concentrated to removed methanol. The aqueous layer was washed with EtOAc (2×5 mL) and acidified with 3N HCl. The mixture was then extracted with EtOAc (3×6 mL). The extracts were combined and dried over sodium sulfate and concentrated to give a white solid. 649 mg.

Workup

  1. customThe reaction was quenched with addition of water
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto removed methanol
  5. washThe aqueous layer was washed with EtOAc (2×5 mL)
  6. extractionThe mixture was then extracted with EtOAc (3×6 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a white solid

Sources & evidence

ORD record
ord-d55a56819ec048738cb97d287a1089e9
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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