Lithium hydroxide, monohydrate → HCID 66985259, compound

HRID 2191541Notes

Reaction equation

HRID 2191541 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]([CH3:22])([CH3:21])[CH2:9]2)=[CH:4][C:3]=1[F:23].[OH:24][Li].O>C1COCC1.CO.O>[C:17]([O:16][C:14]([NH:11][C:10]([CH3:22])([CH3:21])[CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:23])[CH:4]=1)[C:12]([OH:24])=[O:13])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66985397HCID 66985397, compound

Product 1

HCID 66985259HCID 66985259, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(4-chloro-3-fluorophenyl)-2,2-dimethyl-5-oxopyrrolidine-1-carboxylate (1.168 g, 3.42 mmol, theor.) was dissolved in 4 mL of each: THF, MeOH, water. The LiOH—H2O (574 mg, 13.7 mmol) was added in one sum to the stirring solution. The reaction mixture was allowed to stir to completion overnight. The reaction mixture was concentrated, and the residue was partitioned between ether and water. The aqueous portion was washed again with ether (both discarded) and then treated with 3N HCl solution until a pH of about 2 to about 3 was achieved. The aqueous portion was extracted with ether several times, and the organics were combined. The organic portion was washed with brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford 4-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorophenyl)-4-methylpentanoic acid as a white solid (1.06 g, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ether and water
  3. washThe aqueous portion was washed again with ether (
  4. additionthen treated with 3N HCl solution until a pH of about 2 to about 3
  5. extractionThe aqueous portion was extracted with ether several times
  6. washThe organic portion was washed with brine
  7. customseparated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8b5bb27f7b443fcb7e02b4b09fdcea5
Source dataset
uspto-grants-2012_12
Patent number
US08329701B2

Reaction notes

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