1,2-Dimethoxyethane → HCID 66975737, compound

HRID 1022686Notes

Reaction equation

HRID 1022686 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.[OH-].[Na+].[CH2:27]([CH2:30][O:31]C)[O:28]C>>[Cl:17][C:12]1[CH:11]=[C:10]([C@@H:9]2[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][C@H:3]2[CH2:2][NH:1][C:27](=[O:28])[CH2:30][OH:31])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 66975351HCID 66975351, compound

Product 1

HCID 66975737HCID 66975737, compound

Procedure

To a solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (171 mg) in dimethoxyethane (3 mL) was added 1 N aqueous sodium hydroxide solution (0.72 ml), and the mixture was stirred overnight. The solvent was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexane) to give the title compound (157 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e52affe2c7af45669537936cdc042f03
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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