Trifluoroacetic acid → HCID 59722656, compound

HRID 1664827Notes

Reaction equation

HRID 1664827 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C@@H:11]1[CH2:17][CH2:16][C@@H:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=2[F:25])[CH2:14][N:13](CC2C=CC(OC)=CC=2OC)[C:12]1=[O:37])[CH:9]=[CH2:10].C([C@H]1CC[C@H](C2C=CC=C(F)C=2F)CN(CC2C=CC(OC)=CC=2OC)C1=O)C=C>ClCCl>[CH2:8]([CH:11]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=2[F:25])[CH2:14][NH:13][C:12]1=[O:37])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67438540HCID 67438540, compoundHCID 67439552HCID 67439552, compound

Product 1

HCID 59722656HCID 59722656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (35 mL) was added to a solution of (3S,6S)-3-allyl-6-(2,3-difluorophenyl)-1-(2,4-dimethoxybenzyl)azepan-2-one and (3R,6R)-3-allyl-6-(2,3-difluorophenyl)-1-(2,4-dimethoxybenzyl)azepan-2-one (3.39 g, 8.15 mol) in dichloromethane (25 mL). After 2.5 h, the reaction mixture was concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. Purification by silica gel chromatography (98.5% dichloromethane/methanol→97% dichloromethane/methanol) gave the mixture of racemic trans compounds (3S,6S)-3-allyl-6-(2,3-difluorophenyl)azepan-2-one and (3R,6R)-3-allyl-6-(2,3-difluorophenyl)azepan-2-one and racemic cis compounds (3S,6R)-3-allyl-6-(2,3-difluorophenyl)azepan-2-one and (3R,6S)-3-allyl-6-(2,3-difluorophenyl)azepan-2-one. MS 266.1 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with ethyl acetate (3×)
  4. washThe organic extracts were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbac63b1e5c74bf29e28b99b82edaa4f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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