Tetrahydrofuran → methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate

HRID 1615738Notes

Reaction equation

HRID 1615738 reaction equation
[CH2:1]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][C:24]([C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=1)=[N:25][OH:26].C(=O)([O-])[O-].[K+].[K+].C1COCC1>C(OCC)(=O)C.O>[CH2:1]([N:8]([CH2:23][C:24]([C:27]1[CH:28]=[C:29]([F:34])[CH:30]=[C:31]([F:33])[CH:32]=1)=[N:25][OH:26])[C@@H:9]([CH2:14][CH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 68790091methyl (S)-2-benzylamino-3-cycloheptyl-propionateHCID 866685372-Bromo-1-(3,5-difluoro-phenyl)-ethanone oxime

Product 1

HCID 86668536methyl (S)-2-(benzyl-{2-(3,5-difluoro-phenyl)-2-[hydroxyimino]-ethyl}-amino)-3-cycloheptyl-propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

820 mg (2.83 mmol) methyl (S)-2-benzylamino-3-cycloheptyl-propionate were stirred overnight at RT together with 0.71 g (2.83 mmol) 2-bromo-1-(3,5-difluoro-phenyl)-ethanone-oxime, 0.51 g (3.68 mmol) potassium carbonate and 10 ml THF. After the addition of water and ethyl acetate the organic phases were combined, washed with water, dried and evaporated to dryness by rotary evaporation. The residue was purified by RP-HPLC. The product-containing fractions were combined, the organic solvent was removed and the aqueous residue was made alkaline with saturated, aqueous sodium hydrogen carbonate solution. It was extracted with ethyl acetate, the organic phase was dried and concentrated by rotary evaporation.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated to dryness by rotary evaporation
  4. customThe residue was purified by RP-HPLC
  5. customthe organic solvent was removed
  6. extractionIt was extracted with ethyl acetate
  7. customthe organic phase was dried
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-3f504e3fa327430fa0b4fc7912954d4f
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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