Di-tert-butyl dicarbonate → (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(3-(1-(5-chloropyrimidin-2-yl)cyclopropyl)-2-oxooxazolidin-5-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate

HRID 513899노트

반응식

HRID 513899 반응식
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:46])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:45])[CH2:12][CH2:13][C@@:14]3([CH:31]([OH:44])[CH2:32][NH:33][C:34]4([C:37]5[N:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=5)[CH2:36][CH2:35]4)[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:48])[CH3:47])(=[O:3])[CH3:2].[O:49](C(OC(C)(C)C)=O)[C:50](OC(C)(C)C)=O>ClCCl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:46])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:45])[CH2:12][CH2:13][C@@:14]3([CH:31]4[O:44][C:50](=[O:49])[N:33]([C:34]5([C:37]6[N:38]=[CH:39][C:40]([Cl:43])=[CH:41][N:42]=6)[CH2:36][CH2:35]5)[CH2:32]4)[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:48])[CH3:47])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 90495Di-tert-butyl dicarbonateHCID 86690394(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((1-(5-chloropyrimidin-2-yl)cyclopropyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate

생성물 1

HCID 86690396(3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(3-(1-(5-chloropyrimidin-2-yl)cyclopropyl)-2-oxooxazolidin-5-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate수율 84.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((1-(5-chloropyrimidin-2-yl)cyclopropyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate (106) (400 mg, 0.588 mmol) in dichloromethane (15 ml) stirred at rt was added BOC2O (1.365 ml, 5.88 mmol). The reaction mixture was stirred at rt overnight then evaporated under reduced pressure and the residue was subjected to a silica gel chromatography with petroleum ether/EtOAc (6:1 to 3:1) to give (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(3-(1-(5-chloropyrimidin-2-yl)cyclopropyl)-2-oxooxazolidin-5-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate (107) (350 mg, 0.496 mmol, 84% yield) as a white solid.

후처리

  1. customthen evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-a2d192e88e2e4c0f81332e7df2b96907
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102685B2

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