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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 513901
[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]
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Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7e54c3ffce39419f9233c802bfd9d029
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102685B2

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