Trifluoroacetic acid → (3R,6S)-3-Amino-6-(2,3-difluorophenyl)azepane-2-thione

HRID 14392

Reaction equation

HRID 14392 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][NH:21][C:20](=[S:23])[C@H:19]([NH:24]C(=O)OC(C)(C)C)[CH2:18][CH2:17]1>ClCCl>[NH2:24][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][NH:21][C:20]1=[S:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59734935tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate

Product 1

HCID 86620123(3R,6S)-3-Amino-6-(2,3-difluorophenyl)azepane-2-thioneYield 99,885.398%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL, 49.6 mmol) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate (680 mg, 1.91 mmol) in dichloromethane (10 mL). After 1 h, the reaction was concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to give the title compound (489 g). MS 257.0 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5368849998c845f2bb88f9e9f2d1f3d9
Source dataset
uspto-grants-2010_06
Patent number
US07732438B2

Linked notes

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