Acetic Acid → 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(N-methylbenzylaminomethyl)indol-2-yl]isoindolinone

HRID 21290

반응식

HRID 21290 반응식
[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([CH:26]=O)=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:4])=[O:3].[CH3:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([CH2:26][NH:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:4])=[O:3].[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([CH2:26][N:37]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:36])=[CH:21][CH:20]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:35])(=[O:3])=[O:4]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7669N-MethylbenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866283014-Methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

생성물 2

HCID 866283074-Methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(benzylaminomethyl)indol-2-yl]isoindolinone수율 19%HCID 866283084-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(N-methylbenzylaminomethyl)indol-2-yl]isoindolinone수율 60%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (100 mg, 0.200 mmol) was dissolved in acetonitrile (5.8 mL), and the solution was treated with N-methylbenzylamine (0.258 mL, 2.00 mmol), acetic acid (0.229 mL, 4.00 mmol) and sodium triacetoxyborohydride (127 mg, 0.599 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(benzylaminomethyl)indol-2-yl]isoindolinone (22.6 mg, yield 19%) and 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(N-methylbenzylaminomethyl)indol-2-yl]isoindolinone (72.1 mg, yield 60%).

후처리

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=20/1)

출처 및 근거

ORD 기록
ord-11e9601f9c9f46ffa2eb8f844bc228fc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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