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

HRID 1022606Notes

Reaction equation

HRID 1022606 reaction equation
Cl.C(O)C.[Cl:5][C:6]1[CH:7]=[C:8]([C@@H:13]2[O:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][C@H:14]2[CH2:27][N:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]3[NH:38][C:37](=[O:39])[O:36][N:35]=3)[C:29]2=[O:40])[CH:9]=[CH:10][C:11]=1[Cl:12]>C(O)C>[ClH:5].[Cl:5][C:6]1[CH:7]=[C:8]([C@@H:13]2[O:19][CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[CH2:27][N:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]3[NH:38][C:37](=[O:39])[O:36][N:35]=3)[C:29]2=[O:40])[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 136340695tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-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 1363406961-{[(6S,7R)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]methyl}-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-2(1H)-one monohydrochlorideYield 186.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 14 N hydrogen chloride-ethanol solution (2 mL, 28.00 mmol) was added to a solution of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-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 (795 mg, 1.48 mmol) in ethanol (8 mL). The reaction mixture was stirred at room temperature for 3 hr, and at 80° C. for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was collected by filtration, and washed with ethanol-hexane to give the title compound (655 mg, 1.383 mmol, 93%).

Workup

  1. waitat 80° C. for 15 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationthe residue was collected by filtration
  4. washwashed with ethanol-hexane

Sources & evidence

ORD record
ord-6ba9076f3c6c4117bcd6752f132e6ed3
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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