Dichloromethane → (E)-7-(2-Carboxy-vinyl)-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepine-4-carboxylic acid benzyl ester hydrochloride

HRID 1711845ノート

反応式

HRID 1711845 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][C:16]2[CH:18]=[C:19](/[CH:22]=[CH:23]/[C:24]([O:26]C(C)(C)C)=[O:25])[CH:20]=[N:21][C:15]=2[NH:14][C:13](=[O:31])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:40]>CCOCC>[ClH:40].[CH2:1]([O:8][C:9]([N:11]1[CH2:17][C:16]2[CH:18]=[C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])[CH:20]=[N:21][C:15]=2[NH:14][C:13](=[O:31])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59456961(E)-7-(2-tert-Butoxycarbonyl-vinyl)-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepine-4-carboxylic acid benzyl ester

生成物 1

HCID 66967367(E)-7-(2-Carboxy-vinyl)-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepine-4-carboxylic acid benzyl ester hydrochloride収率 91%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of (E)-7-(2-tert-butoxycarbonyl-vinyl)-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepine-4-carboxylic acid benzyl ester (0.31 g, 0.73 mmol) in CH2Cl2 (5 mL) was treated with TFA (5 mL). After stirring at room temperature for 30 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl (10 mL of a 4.0 M solution in dioxane, 40 mmol) to give a cloudy mixture. The mixture was diluted with Et2O (200 mL) to give an off-white precipitate. After stirring for 15 min, the solid was isolated by filtration, washed with Et2O, and dried under vacuum for 1.5 h to give the title compound (0.27 g, 91%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.50-10.47 (m, 1H), 8.49 (s, 1H), 8.09-8.15 (m, 1H), 7.53-7.59 (m, 1H), 7.15-7.33 (m, 5H), 6.51-6.65 (m, 1H), 5.42 (bs, 2H), 5.05-5.08 (m, 2H), 4.63 (s, 2H), 4.43 (s, 2H); MS (ESI) m/e 368 (M+H)+.

後処理

  1. concentrationthe clear tan solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous HCl (10 mL of a 4.0 M solution in dioxane, 40 mmol)
  3. customto give a cloudy mixture
  4. customto give an off-white precipitate
  5. stirringAfter stirring for 15 min
  6. customthe solid was isolated by filtration
  7. washwashed with Et2O
  8. customdried under vacuum for 1.5 h

出典と根拠

ORDレコード
ord-d3649a448950458597e717b3f7e70039
出典データセット
uspto-grants-2010_09
特許番号
US07790709B2

反応ノート

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