Ethanol hydrochloride → 1-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}pyridin-2(1H)-one monohydrochloride

HRID 1022633Notes

Reaction equation

HRID 1022633 reaction equation
Cl.C(O)C.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[O:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]2[CH2:26][N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[O:33])=[CH:8][C:7]=1[F:34]>C(O)C>[ClH:5].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[O:18][CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[CH2:26][N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[O:33])=[CH:8][C:7]=1[F:34]

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 66976191HCID 66976191, compound

Product 1

HCID 669755911-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}pyridin-2(1H)-one monohydrochlorideYield 199.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14 N Hydrogen chloride-ethanol solution (1 mL, 14.00 mmol) was added to a solution (3 mL) of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-[(2-oxopyridin-1(2H)-yl)methyl]-1,4-oxazepane-4-carboxylate (267 mg, 0.61 mmol) in ethanol, and the mixture was stirred at room temperature for 3 hr. The residue was concentrated, diethyl ether was added, and the mixture was stirred for a while. The insoluble material was collected by filtration to give the title compound (227 mg, 0.608 mmol, 100%).

Workup

  1. concentrationThe residue was concentrated
  2. additiondiethyl ether was added
  3. stirringthe mixture was stirred for a while
  4. filtrationThe insoluble material was collected by filtration

Sources & evidence

ORD record
ord-c998a7ed3ad149dbaaf2997d30a1a1cb
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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