Sodium Thiosulfate → HCID 67959407, compound

HRID 1404991Notes

Reaction equation

HRID 1404991 reaction equation
[CH:1]1([C:4]2[C:13]3[O:12][CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=3[S:6][CH:5]=2)[CH2:3][CH2:2]1.[Br:21]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[Br:21][C:5]1[S:6][C:7]2[CH2:8][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:11][O:12][C:13]=2[C:4]=1[CH:1]1[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 67959129HCID 67959129, compound

Product 1

HCID 67959407HCID 67959407, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 8-cyclopropyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (375 mg) obtained in Example 3, step 1, N-bromosuccinimide (237 mg) and acetonitrile (3 ml) was stirred at room temperature for 2 hr, 10% aqueous sodium thiosulfate solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 2→10% ethyl acetate/hexane) to give the title compound (359 mg, 75%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 2→10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c5e80924d7d942428085d470e7a65e53
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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