N-Methoxy-N-methyl-2-phenylacetamide → HCID 66665381, compound

HRID 872298Notes

Reaction equation

HRID 872298 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:14][CH:12]([CH2:13]2)[O:11][C:10](=[O:15])[NH:9]3)=[CH:4][CH:3]=1.[Li]CCCC.CON(C)[C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CCCCCC>[C:26]1([CH2:25][C:24]([C:2]2[CH:7]=[CH:6][C:5]([C:8]34[CH2:14][CH:12]([CH2:13]3)[O:11][C:10](=[O:15])[NH:9]4)=[CH:4][CH:3]=2)=[O:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 10419762N-Methoxy-N-methyl-2-phenylacetamideHCID 58229900HCID 58229900, compoundHCID 178418339Butyllithium2×

Product 1

HCID 66665381HCID 66665381, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

A solution of 5-(4-bromo-phenyl)-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one (prepared according to WO2009/148916, 4 g) in dry THF (60 mL) was cooled to −78° C. and treated with n-BuLi (6.56 mL of a 2.5M solution in hexane) and stirred for 30 minutes at this temperature before addition of further n-BuLi (13.1 mL of a 2.5M solution in hexane). Stirring was continued at this temperature for 30 minutes before a solution of N-methoxy-N-methyl-benzeneacetamide (prepared according to US6407119B1, 4.6 g) in THF (10 mL) was added. After 10 minutes the reaction was quenched with saturated aqueous ammonium chloride solution, extracted with EtOAc and the combined organic phases washed with brine, filtered and concentrated. The residue was triturated with hexane/EtOAc to give the title compound which was used in the next step without further purification.

Workup

  1. additionwas added
  2. customAfter 10 minutes the reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with EtOAc
  4. washthe combined organic phases washed with brine
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with hexane/EtOAc

Sources & evidence

ORD record
ord-390350192f2947f3b4acc0ccb2377f88
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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