Fumaric Acid → N-[(6R,7S)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]acetamide monofumarate

HRID 1022621Notes

Reaction equation

HRID 1022621 reaction equation
[C:1]([NH:4][C@H:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[O:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)(=[O:3])[CH3:2].C(OCC)(=O)C.Cl.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>C(O)C>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[Cl:19][C:14]1[CH:13]=[C:12]([C@@H:11]2[O:10][CH2:9][CH2:8][NH:7][CH2:6][C@H:5]2[NH:4][C:1](=[O:3])[CH3:2])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 3

HCID 444972Fumaric AcidHCID 21866389Hydrogen chloride-ethyl acetateHCID 66975754tert-butyl (6R,7S)-6-(acetylamino)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 86663854N-[(6R,7S)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]acetamide monofumarateYield 106.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl (6R,7S)-6-(acetylamino)-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 1 hr. The residue obtained by concentration under reduced pressure was desalted by a solid phase extraction resin (column: PL StrastoSphere solid phase extraction resin (PL-HCO3 MP StratoSpheres™), 500 mg, StrastoSphere, mobile phase: methanol). To a solution of the residue obtained by concentration under reduced pressure in ethanol was added a solution of fumaric acid (33.7 mg) in ethanol. The mixture was concentrated under reduced pressure to give the title compound (130 mg).

Workup

  1. customThe residue obtained by concentration under reduced pressure
  2. extractionwas desalted by a solid phase extraction resin (column
  3. extractionPL StrastoSphere solid phase extraction resin (PL-HCO3 MP StratoSpheres™), 500 mg
  4. customTo a solution of the residue obtained by concentration under reduced pressure in ethanol
  5. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8aa8d611b2354113bb13f33cf758fbdb
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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