Water → tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[3-(hydrazinocarbonyl)-2-oxopyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022822Notes

Reaction equation

HRID 1022822 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([O:31]C)=O)[C:24]2=[O:33])=[CH:4][C:3]=1[F:34].O.[NH2:36][NH2:37].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:36][NH2:37])=[O:31])[C:24]2=[O:33])=[CH:4][C:3]=1[F:34]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 66975246HCID 66975246, compound

Product 1

HCID 66975927tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[3-(hydrazinocarbonyl)-2-oxopyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylateYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[3-(methoxycarbonyl)-2-oxopyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate (155.7 mg) in ethanol (1.5 mL) was added hydrazine monohydrate (79 mg) at room temperature, and the mixture was heated under reflux for 2 days. The reaction mixture was allowed to cool to room temperature, and poured into water, and the mixture was partitioned with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (138 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 days
  3. customthe mixture was partitioned with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b6a8bce2172424ba360ee1fe3c7423f
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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