Citric Acid → HCID 68278269, compound

HRID 1022655Notes

Reaction equation

HRID 1022655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@@H:10]2[CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([O:33]C)=[O:32])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:19]([O:18][C:16]([N:12]1[CH2:11][C@H:10]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([OH:33])=[O:32])[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 66975238HCID 66975238, compound

Product 1

HCID 68278269HCID 68278269, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (6R*,7R*)-7-(3,4-dichlorophenyl)-6-{[2-(methoxycarbonyl)phenoxy]methyl}-1,4-oxazepane-4-carboxylate (160 mg) in methanol (2 mL) was added 8 N aqueous sodium hydroxide solution (1 mL) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (110 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-177ac08965a2412fb939cb3cabb99720
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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