Hydrogen chloride-ethyl acetate → N-[(6R,7S)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]sulfamide monohydrochloride

HRID 1022623Notes

Reaction equation

HRID 1022623 reaction equation
C(OC([NH:8][S:9]([NH:12][C@H:13]1[C@H:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[O:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)(=[O:11])=[O:10])=O)(C)(C)C.C(OCC)(=O)C.Cl>>[ClH:26].[Cl:27][C:22]1[CH:21]=[C:20]([C@@H:19]2[O:18][CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[NH:12][S:9]([NH2:8])(=[O:10])=[O:11])[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66976162tert-butyl (6R,7S)-6-{[(tert-butoxycarbonyl)sulfamoyl]amino}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976255N-[(6R,7S)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]sulfamide monohydrochlorideYield 150.7%

Procedure

To tert-butyl (6R,7S)-6-{[(tert-butoxycarbonyl)sulfamoyl]amino}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) was added 4.0 M hydrogen chloride-ethyl acetate solution (4 mL), and the mixture was stirred at room temperature for 2 hr. The residue obtained by concentration under reduced pressure was washed with ethyl acetate-hexane to give the title compound (105 mg).

Workup

  1. customThe residue obtained by concentration under reduced pressure
  2. washwas washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-9c43bde22493430b8a5531538969e093
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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