Water → HCID 66975177, compound

HRID 1022790Notes

Reaction equation

HRID 1022790 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16]I)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][NH:38][CH2:37][C:36]3[CH:39]=[CH:40][C:33]([O:32][CH3:31])=[CH:34][CH:35]=3)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 66976424HCID 66976424, compound

Product 1

HCID 66975177HCID 66975177, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-(iodomethyl)-1,4-oxazepane-4-carboxylate (1.4 g) in DMF (5 mL) were added potassium carbonate (1.2 g) and 4-methoxybenzylamine (0.79 g), and the mixture was stirred at 80° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (650 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-13185f98701d471095c8467a66225b1f
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…