Lithium Hydroxide → HCID 57974071, compound

HRID 1864833Notes

Reaction equation

HRID 1864833 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18]CC)=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[O:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([OH:18])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[O:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86616389HCID 86616389, compound

Product 1

HCID 57974071HCID 57974071, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [(5R)-5-(3,5-difluorophenyl)-2,2-dimethyl-3-oxomorpholin-4-yl]acetate from Step H (150 mg, 0.46 mmol) in THF (3 mL) and H2O (3 mL) was added 1 N aqueous LiOH (0.55 mL, 0.55 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H-90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=300 (M+1).

Workup

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-6ef4443a12eb4333850852390f4fd989
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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