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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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1,2-Dichloroethane → 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-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) 2,2-dimethylsuccinate

HRID 513901
ノート
印刷プレビュー

反応式

HRID 513901 の反応式
[C:1]([O:5][C:6](=[O:14])[C:7]([CH3:13])([CH3:12])[CH2:8][C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[N:18][C:19]([C:22]2([N:25]3[CH2:29][CH:28]([C@:30]45[CH2:56][C:55](=[O:57])[C:54]([CH:58]([CH3:60])[CH3:59])=[C:31]4[C@@H:32]4[C@@:45]([CH3:48])([CH2:46][CH2:47]5)[C@@:44]5([CH3:49])[C@@H:35]([C@:36]6([CH3:53])[C@@H:41]([CH2:42][CH2:43]5)[C:40]([CH3:51])([CH3:50])[C@@H:39]([OH:52])[CH2:38][CH2:37]6)[CH2:34][CH2:33]4)[O:27][C:26]3=[O:61])[CH2:24][CH2:23]2)=[N:20][CH:21]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:12][C:7]([CH3:13])([CH2:8][C:9]([O:11][C@H:39]1[CH2:38][CH2:37][C@@:36]2([CH3:53])[C@@H:41]([CH2:42][CH2:43][C@:44]3([CH3:49])[C@@H:35]2[CH2:34][CH2:33][C@H:32]2[C@@:45]3([CH3:48])[CH2:46][CH2:47][C@@:30]3([C@@H:28]4[O:27][C:26](=[O:61])[N:25]([C:22]5([C:19]6[N:18]=[CH:17][C:16]([Cl:15])=[CH:21][N:20]=6)[CH2:23][CH2:24]5)[CH2:29]4)[CH2:56][C:55](=[O:57])[C:54]([CH:58]([CH3:60])[CH3:59])=[C:31]32)[C:40]1([CH3:51])[CH3:50])=[O:10])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:14].[CH3:12][C:7]([CH3:13])([CH2:8][C:9]([O:52][C@H:39]1[CH2:38][CH2:37][C@@:36]2([CH3:53])[C@@H:41]([CH2:42][CH2:43][C@:44]3([CH3:49])[C@@H:35]2[CH2:34][CH2:33][C@H:32]2[C@@:45]3([CH3:48])[CH2:46][CH2:47][C@@:30]3([C@H:28]4[O:27][C:26](=[O:61])[N:25]([C:22]5([C:19]6[N:20]=[CH:21][C:16]([Cl:15])=[CH:17][N:18]=6)[CH2:24][CH2:23]5)[CH2:29]4)[CH2:56][C:55](=[O:57])[C:54]([CH:58]([CH3:59])[CH3:60])=[C:31]32)[C:40]1([CH3:50])[CH3:51])=[O:10])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 111,2-DichloroethaneHCID 235551774-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoic acidHCID 866903953-(1-(5-chloropyrimidin-2-yl)cyclopropyl)-5-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-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-3a-yl)oxazolidin-2-one

生成物 2

HCID 86690397
1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-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) 2,2-dimethylsuccinate
HCID 866903981-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-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) 2,2-dimethylsuccinate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 4-tert-butoxy-3,3-dimethyl-4-oxobutanoic acid 10 (119 mg, 0.587 mmol), 3-(1-(5-chloropyrimidin-2-yl)cyclopropyl)-5-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-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-3a-yl)oxazolidin-2-one (108) (130 mg, 0.196 mmol), EDC (188 mg, 0.978 mmol) and DMAP (71.7 mg, 0.587 mmol) in DCM (5 mL) was stirred at rt overnight. After the reaction finished, the mixture was diluted with DCM (25 ml), washed with water (2×15 ml) and brine (20 ml), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/EtOAc (6:1 to 3:1) as eluent to give the two diastereomeric products 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-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) 2,2-dimethylsuccinate (109) and 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-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) 2,2-dimethylsuccinate (110) in the amounts of (80 mg, 45%) and (50 mg, 22%) as white solids. The stereochemical assignments for each diastereomer were not made. Compound A (tentatively designated as 109): LC/MS: m/z calculated 847.5. found 848.3 (M+1)+. Compound B (tentatively designated as 110): LC/MS: m/z calculated 847.5. found 848 (M+1)+.

後処理

  1. washwashed with water (2×15 ml) and brine (20 ml)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-7e54c3ffce39419f9233c802bfd9d029
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102685B2

反応ノート

読み込み中…

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