Ethanol hydrochloride → 1-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2(1H)-one monohydrochloride

HRID 1022636Notes

Reaction equation

HRID 1022636 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]=[C:29]([C:33]3[NH:37][C:36](=[O:38])[O:35][N:34]=3)[C:28]2=[O:39])=[CH:8][C:7]=1[F:40]>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]=[C:29]([C:33]3[NH:37][C:36](=[O:38])[O:35][N:34]=3)[C:28]2=[O:39])=[CH:8][C:7]=1[F:40]

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 136340698tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[2-oxo-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate

Product 1

HCID 1363406991-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2(1H)-one monohydrochlorideYield 185.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

14 N Hydrogen chloride-ethanol solution (0.5 ml, 7.00 mmol) was added to a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-{[2-oxo-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-1(2H)-yl]methyl}-1,4-oxazepane-4-carboxylate (180 mg, 0.35 mmol) in ethanol (2 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethanol (4 ml), and the mixture was heated under reflux for 10 min. The precipitated crystals were collected by filtration to give the title compound (149 mg, 0.325 mmol, 94%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 min
  3. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-1694433ca2e54aa5ab41394531f71f37
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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