Trifluoroacetic acid → (3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-[2-(methylthio)ethyl]azepan-2-one

HRID 271929

Reaction equation

HRID 271929 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]([CH2:23][CH2:24][S:25][CH3:26])[C:20](=[O:27])[C@H:19]([NH:28]C(=O)OC(C)(C)C)[CH2:18][CH2:17]1>ClCCl>[NH2:28][C@@H:19]1[CH2:18][CH2:17][C@@H:16]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([F:15])[C:9]=2[F:8])[CH2:22][N:21]([CH2:23][CH2:24][S:25][CH3:26])[C:20]1=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86595038tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-1-[2-(methylthio)ethyl]-2-oxoazepan-3-ylcarbamate

Product 1

HCID 60037859(3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-[2-(methylthio)ethyl]azepan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-1-[2-(methylthio)ethyl]-2-oxoazepan-3-ylcarbamate (77 mg, 0.186 mmol) in dichloromethane (10 mL). After 30 min, the solution was concentrated and azeotroped with toluene (2×). Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. MS 315.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-bd21744596284124b7df4062af8967d3
Source dataset
uspto-grants-2008_11
Patent number
US07452903B2

Linked notes

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