Trifluoroacetic acid → ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

HRID 2376144ノート

反応式

HRID 2376144 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13](C(OC(C)(C)C)=O)[C:14]2[N:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:18][CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl.CCOC(C)=O.O>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[N:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:18][CH:19]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 86603754ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-pyrrolidinyl](tert-butoxycarbonyl)amino}-2-pyrazinyl)acrylate

生成物 1

HCID 86603676ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate収率 85%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

To an ice-cooled solution of ethyl (2E)-3-(5-{[(3R)-1-benzyl-3-pyrrolidinyl](tert-butoxycarbonyl)amino}-2-pyrazinyl)acrylate (4.63 g) in dichloromethane (7.8 ml) were added anisole (4.7 ml) and trifluoroacetic acid (15.6 ml), the mixture was stirred at 25° C. for 3.5 hours. The mixed solution was poured into a mixture of water and AcOEt. The pH of the aqueous layer was adjusted to ca.8 with NaHCO3. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give crude powder. The resulting residue was purified by column chromatography on silica gel (50 g) using a mixed solvent of CH2Cl2 and MeOH (100:1 to 20:1). The fractions containing the objective compound were collected and evaporated under reduced pressure. Title compound (3.05 g, 85%) was obtained as slightly yellowish powder.

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customto give crude powder
  6. customThe resulting residue was purified by column chromatography on silica gel (50 g)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-be17276b5b3f43f2a9cb73da736517e1
出典データセット
uspto-grants-2008_12
特許番号
US07465731B2

反応ノート

読み込み中…