Bromide ion → HCID 58485255, compound

HRID 2091524Notes

Reaction equation

HRID 2091524 reaction equation
[C:1]([S@:5](/[N:7]=[C:8](/[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)\[CH2:9][CH2:10][N:11]([C@H:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH3:20])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Br-].[CH2:33]1[CH2:37]OC[CH2:34]1>>[CH3:22][C:21]([CH3:24])([CH3:23])[C@@H:19]([N:11]([CH2:10][CH2:9][C@@:8]([NH:7][S@@:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[O:6])([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[CH2:37][CH:33]=[CH2:34])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[CH3:20]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 58485262HCID 58485262, compound

Product 1

HCID 58485255HCID 58485255, compound

Procedure

To a solution of tert-butyl (E)-3-((R)-tert-butylsulfinylimino)-3-(4-fluorophenyl)propyl((S)-3,3-dimethylbutan-2-yl)carbamate (800 mg, 1.76 mmol) in THF (10 mL) was added allymagnesium bromide (1 M, 6 mL, 5.29 mmol) dropwise at −78° C. under N2. After adding completely, the reaction mixture was stirred at rt for 2 h. The reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give tert-butyl (S)-3,3-dimethylbutan-2-yl((R)-3-((R)-1,1-dimethylethylsulfinamido)-3-(4-fluorophenyl)hex-5-enyl)carbamate (870 mg, crude), which was used for the next step without further purification.

Workup

  1. additionAfter adding completely
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-49baf2cfccea473eb409f7e3d8f2b995
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

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