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ノート

反応式

HRID 33995 の反応式
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

参加物

5

反応物 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

生成物 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 acid収率 88%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca92106cd02a42e6852eae3392adf4e6
出典データセット
uspto-grants-2008_09
特許番号
US07429658B2

反応ノート

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