(S)-benzyl 4-bromo-1-(3,5-dichlorophenyl)-3-oxobutan-2-ylcarbamate → HCID 86622360、化合物

HRID 501747ノート

反応式

HRID 501747 の反応式
[Br:1][CH2:2][C:3](=[O:25])[C@@H:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1>C1COCC1.C(O)C>[Br:1][CH2:2][C@@H:3]([OH:25])[C@@H:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]1[CH:7]=[C:8]([Cl:13])[CH:9]=[C:10]([Cl:12])[CH:11]=1

参加物

4

反応物 1

HCID 86622361(S)-benzyl 4-bromo-1-(3,5-dichlorophenyl)-3-oxobutan-2-ylcarbamate

生成物 1

HCID 86622360HCID 86622360、化合物収率 80%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

Step BF (6): A 1M solution of LiAlH(OtBu)3 in THF (22.9 mL, 22.9 mmol) was diluted with THF (30.5 mL) and ethanol (56 mL) and cooled to −78° C. A solution of (S)-benzyl 4-bromo-1-(3,5-dichlorophenyl)-3-oxobutan-2-ylcarbamate (5.093 g, 11.45 mmol) in THF (56 mL) was then added dropwise down the side of the flask. After 15 min, TLC indicated no starting material remained. The reaction was carefully quenched with 1M HCl and let warm to rt. The organic solvents were removed in vacuo. The residue was taken up in EtOAc, and the aluminum salts removed via filtration. The organic layer was dried over MgSO4, and concentrated to afford benzyl (2S,3S)-4-bromo-1-(3,5-dichlorophenyl)-3-hydroxybutan-2-ylcarbamate (4.08 g, 80% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.05-7.50 (m, 9H) 5.55 (d, J=5.80 Hz, 1H) 4.99 (d, J=12.8 Hz, 1H) 4.87 (d, J=12.8 Hz, 1H) 3.66-3.77 (m, 1H) 3.56-3.65 (m, 2H) 3.36-3.45 (m, 1H) 3.01 (dd, J=13.73, 3.05 Hz, 1H) 2.59 (dd, J=13.43, 10.38 Hz, 1H).

後処理

  1. customThe reaction was carefully quenched with 1M HCl
  2. temperaturelet warm to rt
  3. customThe organic solvents were removed in vacuo
  4. customthe aluminum salts removed via filtration
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-7e800ca160cf4d808bfa5191fb99c086
出典データセット
uspto-grants-2010_08
特許番号
US07772221B2

反応ノート

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