Water → HCID 66975990, compound

HRID 1022810Notes

Reaction equation

HRID 1022810 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH:16]3[CH2:18][O:17]3)[O:14][CH2:13][CH2:12][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:26][S-:27].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH:16]([OH:17])[CH2:18][S:27][CH3:26])[O:14][CH2:13][CH2:12][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86663879HCID 86663879, compound2×

Product 1

HCID 66975990HCID 66975990, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of a mixture (420 mg) of tert-butyl (6RS,7RS)-6-(3,4-dichlorophenyl)-7-[(2RS)-oxiran-2-yl]-1,4-oxazepane-4-carboxylate and tert-butyl (6SR,7SR)-6-(3,4-dichlorophenyl)-7-[(2RS)-oxiran-2-yl]-1,4-oxazepane-4-carboxylate in DMF (2 mL) was added sodium thiomethoxide (114 mg), and the mixture was stirred at room temperature for 10 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous potassium carbonate and 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 (130 mg) in a less polar fraction as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous potassium carbonate and 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-aeed6fda090446d9beda8553c77d0cbe
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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