Sodium Bicarbonate → HCID 66976184, compound

HRID 1022765Notes

Reaction equation

HRID 1022765 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][C@H:11]1[C@H:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=2)[O:16][CH2:15][CH2:14][N:13]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:12]1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[CH2:10][C@H:11]1[C@H:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=2)[O:16][CH2:15][CH2:14][N:13]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:12]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66975935HCID 66975935, compound

Product 1

HCID 66976184HCID 66976184, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of tert-butyl (6R,7R)-6-{2-[(2-aminophenyl)amino]-2-oxoethyl}-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (155 mg) in acetic acid (1.1 mL) was stirred at 100° C. for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (128 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with distilled water and 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 chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-34df67d340314c77b41a3201b63125e1
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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