Hydrogen chloride-ethyl acetate → N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-(1-methylethoxy)acetamide monohydrochloride

HRID 1022631Notes

Reaction equation

HRID 1022631 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(OC(C)(C)C)=O)[CH2:10][C@H:9]2[CH2:22][NH:23][C:24](=[O:30])[CH2:25][O:26][CH:27]([CH3:29])[CH3:28])=[CH:4][C:3]=1[F:31].C(OCC)(=O)C.Cl>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:22][NH:23][C:24](=[O:30])[CH2:25][O:26][CH:27]([CH3:28])[CH3:29])=[CH:4][C:3]=1[F:31]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66975815tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-({[(1-methylethoxy)acetyl]amino}methyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976382N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-(1-methylethoxy)acetamide monohydrochlorideYield 92.8%

Procedure

To tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-({[(1-methylethoxy)acetyl]amino}methyl)-1,4-oxazepane-4-carboxylate (384 mg) was added 4.0 M hydrogen chloride-ethyl acetate solution (6.28 ml), and the mixture was stirred at room temperature for 1 hr. The residue obtained by concentration under reduced pressure was crystallized from ethanol-hexane solvent to give the title compound (153.4 mg).

Workup

  1. customThe residue obtained by concentration under reduced pressure
  2. customwas crystallized from ethanol-hexane solvent

Sources & evidence

ORD record
ord-b5eab9b15ca04edb9ccf030bb41e9c1c
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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