Diisopropylethylamine → tert-Butyl (3R,4S)-3-{[[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxy-propyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]phenyl}piperidine-1-carboxylate

HRID 658253노트

반응식

HRID 658253 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[C@@H:10]([C:33]([OH:35])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si:36]([O:43][C:44]1[CH:45]=[C:46]([CH:52]=[C:53]([CH2:55][CH2:56][CH2:57][O:58][CH3:59])[CH:54]=1)[CH2:47][NH:48][CH:49]1[CH2:51][CH2:50]1)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOCC>[Si:36]([O:43][C:44]1[CH:45]=[C:46]([CH:52]=[C:53]([CH2:55][CH2:56][CH2:57][O:58][CH3:59])[CH:54]=1)[CH2:47][N:48]([CH:49]1[CH2:51][CH2:50]1)[C:33]([C@@H:10]1[C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:35])([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57956095N-[3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl]cyclo-propanamineHCID 59234216(3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acid

생성물 1

HCID 86639853tert-Butyl (3R,4S)-3-{[[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxy-propyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]phenyl}piperidine-1-carboxylate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acid (piperidine acid 1) (1 eq) and N-[3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl]cyclo-propanamine (amine 1) (1.8 eq.) in DCM (0.15 M) was added HATU (1.5 eq.) and Hunig's base (3 eq.). After stirring for 18 hr at rt, the reaction was diluted with ether. The organic extract was washed three times with 1 N aqueous HCl, water, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex) to afford the title compound as an oil.

후처리

  1. extractionThe organic extract
  2. washwas washed three times with 1 N aqueous HCl, water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex)

출처 및 근거

ORD 기록
ord-43dc98af8a2b401194bb63835ec3fb9c
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076359B2

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