Sodium Hydroxide → HCID 66705683, compound

HRID 425420Notes

Reaction equation

HRID 425420 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:39]=[CH:38][C:13]([CH2:14][C:15]3([CH3:37])[C:19](=[O:20])[O:18]C(C4C=CC=CC=4)[N:16]3[C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])=[CH:12][CH:11]=2)=[N:8][CH:9]=1>CO.O>[CH2:30]([O:29][C:27]([NH:16][C:15]([CH3:37])([CH2:14][C:13]1[CH:38]=[CH:39][C:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][N:8]=2)=[CH:11][CH:12]=1)[C:19]([OH:20])=[O:18])=[O:28])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66705667HCID 66705667, compound

Product 1

HCID 66705683HCID 66705683, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5N Aqueous sodium hydroxide (1.45 mL) was added to an ambient temperature solution of benzyl 4-[4-(5-fluoropyridin-2-yl)benzyl]-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate (180 mg, 0.36 mmol) in methanol (2 mL) and water (2 mL). After stirring at 80° C. for 2 h, the reaction mixture was concentrated. The residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated in vacuo to afford 2-{[(benzyloxy)carbonyl]amino}-3-[4-(5-fluoropyridin-2-yl)phenyl]-2-methylpropanoic acid which was used in the subsequent step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e1ec64c1f1c43b0b3338d1d7408badd
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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