Water → 4-tert-butyl 7-methyl (6R,7R)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,7-dicarboxylate

HRID 1022807Notes

Reaction equation

HRID 1022807 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[C@H:12]([C:23]([OH:25])=[O:24])[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Cl:22][C:17]1[CH:16]=[C:15]([C@H:13]2[C@H:12]([C:23]([O:25][CH3:26])=[O:24])[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14]2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66976870(6R,7R)-4-(tert-butoxycarbonyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-7-carboxylic acid

Product 1

HCID 866638784-tert-butyl 7-methyl (6R,7R)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,7-dicarboxylateYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (6R,7R)-4-(tert-butoxycarbonyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-7-carboxylic acid (3.11 g) in DMF (10 mL) were added potassium carbonate (1.32 g) and methyl iodide (0.748 mL). The mixture was stirred at room temperature for 2 hr under nitrogen purging, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (2.86 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))

Sources & evidence

ORD record
ord-6d81750b8d7c4e689b72e9fc36a8df02
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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