Carbon tetrabromide → HCID 178463279、化合物

HRID 1527792ノート

反応式

HRID 1527792 の反応式
[C:1]([O:5][C:6]([N:8]([CH3:33])[C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH2:31][CH3:32])[C:16]2[C:17]([CH3:30])=[C:18]([CH:23]=[C:24]([C:26]#[C:27][CH2:28]O)[CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:54]>C(Cl)Cl>[Br:54][CH2:28][C:27]#[C:26][C:24]1[CH:25]=[C:16]([N:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:33])[CH2:10][CH2:11]2)[CH2:31][CH3:32])[C:17]([CH3:30])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178463301HCID 178463301、化合物

生成物 1

HCID 178463279HCID 178463279、化合物収率 38.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of methyl 3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-5-(3-hydroxyprop-1-yn-1-yl)-2-methylbenzoate (1.2 g, 2.62 mmol) in DCM (15 mL), PPh3 (1.37 g, 5.22 mmol) and CBr4 (1.7 g, 5.10 mmol) were added at 0° C. and reaction was stirred for 4 h at room temperature. On completion, reaction was quenched with ice water and extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure. The crude material was purified by column chromatography to afford the title compound (0.5 g, 38.5% yield).

後処理

  1. customreaction
  2. customOn completion, reaction
  3. customwas quenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers were washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography

出典と根拠

ORDレコード
ord-28339db572da4c8a8269b056ca551ff0
出典データセット
uspto-grants-2015_07
特許番号
US09089575B2

反応ノート

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