1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4,5-bis(nitrooxy)pentyl (2Z)-4(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate

HRID 1437607노트

반응식

HRID 1437607 반응식
[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[N+:27]([O:30][CH:31]([CH2:36][O:37][N+:38]([O-:40])=[O:39])[CH2:32][CH2:33][CH2:34]O)([O-:29])=[O:28].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([O:10][CH2:34][CH2:33][CH2:32][CH:31]([O:30][N+:27]([O-:29])=[O:28])[CH2:36][O:37][N+:38]([O-:40])=[O:39])=[O:9])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11617716(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acidHCID 579416234,5-Bis(nitrooxy)pentyl alcohol

생성물 1

HCID 114444494,5-bis(nitrooxy)pentyl (2Z)-4(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate수율 38.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1.72 g of (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 20 mL of CH2Cl2 at 0° C. was added 1.06 g of 4,5-bis(nitrooxy)pentyl alcohol, 225 mg of DMAP and 970 mg of EDCI. The mixture was stirred at RT for 2 h then quenched by addition of NH4Cl sat., extracted with EtOAc, washed with NaHCO3 sat., brine and dried over sodium sulfate. Purification by flash chromatography afforded 1 g of the titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.77 (d, 2H), 7.43 (d, 2H), 7.18-7.16 (m, 3H), 7.08 (dd, 2H), 5.53-5.50 (m, 1H), 5.20 (s, 1H), 4.97 (dd, 1H), 4.69 (dd, 1H), 4.31 (m, 2H), 3.05 (s, 2H), 1.89 (m, 7H).

후처리

  1. customthen quenched by addition of NH4Cl sat.
  2. extractionextracted with EtOAc
  3. washwashed with NaHCO3 sat., brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-03c2848ff5af4a138c5ef799bdecf1e1
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622502B2

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