Trifluoroacetic acid → (3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one

HRID 20145

反応式

HRID 20145 の反応式
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][C:24]([F:27])([F:26])[F:25])[C:20](=[O:28])[C@H:19]([NH:29]C(=O)OC(C)(C)C)[CH2:18][CH2:17]1>ClCCl>[NH2:29][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][C:24]([F:27])([F:25])[F:26])[C:20]1=[O:28]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 865950421,1-Dimethylethyl N-((3R,6S)-6-(2,3-difluorophenyl)hexahydro-2-oxo-1-(2,2,2-trifluoroethyl)-1H-azepin-3-yl)carbamate

生成物 1

HCID 23653826(3R,6S)-3-Amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (2.5 mL) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-ylcarbamate (135 mg, 0.320 mmol) in dichloromethane (5 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 323.1 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.11-7.03 (m, 2H), 6.93-6.89 (m, 1H), 4.21-4.13 (m, 1H), 4.10-3.98 (m, 2H), 3.85 (d, J=11.0 Hz, 1H), 3.35 (d, J=15.4 Hz, 1H), 3.04-2.99 (m, 1H), 2.13-2.09 (m, 2H), 2.08-2.02 (m, 1H), 1.78-1.70 (m, 3H).

後処理

  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

出典と根拠

ORDレコード
ord-f090965564c3415da064c359251392b3
出典データセット
uspto-grants-2010_06
特許番号
US07745427B2

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