Ammonium Chloride → HCID 66976528, compound

HRID 1022787Notes

Reaction equation

HRID 1022787 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([C@H:12]2[C@@H:18]([CH2:19][NH:20][S:21]([CH:24]=[CH2:25])(=[O:23])=[O:22])[O:17][CH2:16][CH2:15][N:14]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11].[Cl-].[NH4+]>CO>[Cl:4][C:5]1[CH:6]=[C:7]([C@H:12]2[C@@H:18]([CH2:19][NH:20][S:21]([CH2:24][CH2:25][O:2][CH3:1])(=[O:23])=[O:22])[O:17][CH2:16][CH2:15][N:14]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 66976868HCID 66976868, compound

Product 1

HCID 66976528HCID 66976528, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

A 28% solution (5 ml) of sodium methoxide in methanol was added dropwise to a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-{[(ethenylsulfonyl)amino]methyl}-1,4-oxazepane-4-carboxylate (235 mg) in methanol (1 mL), and the mixture was stirred at 60° C. overnight. To the reaction mixture was added saturated aqueous ammonium chloride solution, 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 (215 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-86f7f919ef604ded8baf40b385eb3a85
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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