Water → HCID 66975642, compound

HRID 1022782Notes

Reaction equation

HRID 1022782 reaction equation
[OH-].[Na+].C([O:6][C:7]([CH3:35])([CH3:34])[C:8]([NH:10][CH2:11][CH:12]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH:13]1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=1)=[O:9])(=O)C.O>C(O)C>[Cl:33][C:28]1[CH:27]=[C:26]([CH:13]2[CH:12]([CH2:11][NH:10][C:8](=[O:9])[C:7]([OH:6])([CH3:35])[CH3:34])[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)[CH:31]=[CH:30][C:29]=1[Cl:32]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66976215HCID 66976215, compound

Product 1

HCID 66975642HCID 66975642, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 M Aqueous sodium hydroxide solution (0.3 mL) was added dropwise to a solution of tert-butyl (6SR,7RS)-7-({[2-(acetyloxy)-2-methylpropanoyl]amino}methyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (150 mg) in ethanol (5 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (130 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0682ef6758054f4985e0992d5e97be74
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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