Hydrochloric Acid → HCID 86663877, compound

HRID 1022793Notes

Reaction equation

HRID 1022793 reaction equation
C([S:4][CH2:5][C@H:6]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][C@H:7]1[C:20]1[CH:25]=[CH:24][C:23](Cl)=[C:22]([Cl:27])[CH:21]=1)(=O)C.[ClH:28].ClN1C(=[O:35])CCC1=O.[Cl-:37].[Na+].[OH2:39]>C(#N)C>[Cl:28][S:4]([CH2:5][C@H:6]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][C@H:7]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:37])=[C:22]([Cl:27])[CH:21]=1)(=[O:35])=[O:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 57417360Sodium chloride; waterHCID 86663876HCID 86663876, compound

Product 1

HCID 86663877HCID 86663877, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl (6R,7S)-7-[(acetylsulfanyl)methyl]-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (115 mg) in acetonitrile (1.1 mL) were added 1 N hydrochloric acid (0.13 mL) and N-chlorosuccinimide (141 mg), and the mixture was stirred at room temperature for 30 min. To the reaction solution was added brine, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (96 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4fecf9a4497c4c9e8724e65f52923ada
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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