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 1711845노트

반응식

HRID 1711845 반응식
[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

참가 물질

5

반응물 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

생성물 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 hydrochloride수율 91%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d3649a448950458597e717b3f7e70039
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790709B2

반응 노트

불러오는 중…