Pyrrolidine → 2-[4-((11S,11aS)-7,8-Dimethoxy-11-hydroxy-5-oxo-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyloxymethyl)-phenoxycarbonylamino]-pentanedioic acid

HRID 33995

반응식

HRID 33995 반응식
C([O:4][C:5](=[O:49])[CH:6]([NH:15][C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][C:27]([N:29]2[C:35]3[CH:36]=[C:37]([O:42][CH3:43])[C:38]([O:40][CH3:41])=[CH:39][C:34]=3[C:33](=[O:44])[N:32]3[CH2:45][CH2:46][CH2:47][C@H:31]3[C@@H:30]2[OH:48])=[O:28])=[CH:21][CH:20]=1)=[O:17])[CH2:7][CH2:8][C:9]([O:11]CC=C)=[O:10])C=C.N1CCCC1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:41][O:40][C:38]1[C:37]([O:42][CH3:43])=[CH:36][C:35]2[N:29]([C:27]([O:26][CH2:25][C:22]3[CH:21]=[CH:20][C:19]([O:18][C:16]([NH:15][CH:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:5]([OH:49])=[O:4])=[O:17])=[CH:24][CH:23]=3)=[O:28])[C@@H:30]([OH:48])[C@@H:31]3[CH2:47][CH2:46][CH2:45][N:32]3[C:33](=[O:44])[C:34]=2[CH:39]=1

참가 물질

5

반응물 2

HCID 31268PyrrolidineHCID 692552912-[4-((11S,11aS)-7,8-dimethoxy-11-hydroxy-5-oxo-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyloxymethyl)-phenoxycarbonylamino]-pentanedioic acid diallyl ester

생성물 1

HCID 690319812-[4-((11S,11aS)-7,8-Dimethoxy-11-hydroxy-5-oxo-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyloxymethyl)-phenoxycarbonylamino]-pentanedioic acid수율 88%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

A solution of the diallyl ester 45 (0.596 g, 0.95 mmol, 1 eq), Pd(PPh3)4 (0.055 g, 0.047 mmol, 0.05 eq) and pyrrolidine (0.34 g, 0.39 mL, 4.7 mmol, 5 eq) in anhydrous CH2Cl2 (18 mL) was stirred at room temperature for 1 h and the solvent removed in vacuo. The residue was washed with EtOAc (3×15 mL), dissolved in MeOH (15 mL) and passed down an IRC 50, weakly acidic, ion exchange column, eluting with MeOH (80 mL). The solvent was removed in vacuo to give the product as a white foam (0.46 g, 88%). 1H NMR (d6 DMSO) δ 7.95 (d, J=6.25 Hz, 1H), 7.33 (d, J=8 Hz, 2H), 7.10 (m, 3H) 6.73 (s, 1H), 5. 49 (d, J=9.2 Hz, 1H), 5.2 (d, J=12.5 Hz, 1H), 4.89 (d, J=12.75 Hz, 1H), 4.00 (m, 1H), 3.80 (m, 7H), 3.45 (m, 4H) 2.30 (t, J=7.5 Hz, 2H), 1.95 (m, 5H). MS (ES+) 602.2.

후처리

  1. customthe solvent removed in vacuo
  2. washThe residue was washed with EtOAc (3×15 mL)
  3. dissolutiondissolved in MeOH (15 mL)
  4. washweakly acidic, ion exchange column, eluting with MeOH (80 mL)
  5. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-ca92106cd02a42e6852eae3392adf4e6
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429658B2

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