Dimethylformamide → HCID 118939068, compound

HRID 523986Notes

Reaction equation

HRID 523986 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1.[Li+].CCC[CH2-].CN([CH:22]=[O:23])C>C1COCC1>[CH:22]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[CH:4][CH:3]=1)=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 61028n-Butyl lithiumHCID 793484N-((1S)-1-(4-Bromophenyl)ethyl)acetamide

Product 1

HCID 118939068HCID 118939068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 20.0 g (74.3 mmol) (S)—N-(1-(4-bromophenyl)ethyl)acetamid (WO 2012/01107) in 300 mL THF are added dropwise 75.0 mL (187 mmol)N-butyllithium (2.5 M in THF) at −78° C. and stirred for 1 h. 10.0 mL (124 mmol) DMF are added dropwise to the mixture at −78° C. and stirred for 2 h. After that aq. NH4CI solution is added and extracted with EtOAc. The organic layer is dried over Na2SO4, filtered and concentrated by evaporation. The residue is purified by column chromatography (silica gel, MeOH:DCM).

Workup

  1. stirringstirred for 2 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by column chromatography (silica gel, MeOH:DCM)

Sources & evidence

ORD record
ord-7a546480212a47d59db3e05d4054172c
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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