Sodium methanesulfinate → HCID 57656374, compound

HRID 911466Notes

Reaction equation

HRID 911466 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][S:31]([O-:33])=[O:32].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 57656525HCID 57656525, compound

Product 1

HCID 57656374HCID 57656374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the crude 3-tert-butoxycarbonyl-6-(4-bromomethyl-benzylthio)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine in anhydrous DMF (1 mL) under nitrogen, add with string sodium methanesulfinate (400 mg, 3.9 mmol), and continue stirring for 30 min at ambient temperature followed by 2 h at 40° C. Add water, extract three times with EtOAc, wash with brine, dry over anhydrous MgSO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (3:1) to give a clear oil that solidifies on standing to a white solid (118 mg, 61%).

Workup

  1. waitfollowed by 2 h at 40° C
  2. extractionAdd water, extract three times with EtOAc
  3. washwash with brine
  4. dry with materialdry over anhydrous MgSO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (3:1)
  7. customto give a clear oil

Sources & evidence

ORD record
ord-18e5611b45364eeaab35cbd0e20d7272
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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