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Phosphoric Acid → ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methylene)cyclohexanecarboxylate

HRID 1773037
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773037
[NH2:1][C@:2]12[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:36])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([CH:24]=[C:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.P(=O)(O)(O)O.[K].[I-].[K+].Cl[CH2:52][CH2:53][N:54]1[CH2:59][CH2:58][S:57](=[O:61])(=[O:60])[CH2:56][CH2:55]1>C(#N)C>[O:60]=[S:57]1(=[O:61])[CH2:58][CH2:59][N:54]([CH2:53][CH2:52][NH:1][C@:2]23[CH2:39][CH2:38][C@@H:37]([C:40]([CH3:42])=[CH2:41])[C@@H:3]2[C@@H:4]2[C@@:17]([CH3:20])([CH2:18][CH2:19]3)[C@@:16]3([CH3:21])[C@@H:7]([C@:8]4([CH3:36])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:22])([CH3:23])[C:11]([CH:24]=[C:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:10][CH2:9]4)[CH2:6][CH2:5]2)[CH2:55][CH2:56]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 1004Phosphoric AcidHCID 4875Potassium IodideHCID 5462222PotassiumHCID 189487894-(2-chloroethyl)thiomorpholine1,1-dioxideHCID 86731496HCID 86731496, Verbindung

Produkt 1

HCID 86731495
ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methylene)cyclohexanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a sealable flask containing ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methylene)cyclohexanecarboxylate (0.015 g, 0.026 mmol) was added phosphoric acid, potassium salt (0.028 g, 0.130 mmol), potassium iodide (0.013 g, 0.078 mmol) and 4-(2-chloroethyl)thiomorpholine 1,1-dioxide (0.015 g, 0.078 mmol). The mixture was diluted with acetonitrile (1 mL), flushed with nitrogen, sealed, and heated to 100° C. After heating the mixture for 22 h, it was cooled to rt, diluted with water (5 mL), and extracted with dichloromethane (3×5 mL). The organic layers were dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was used in the next step with no additional purification. LCMS: m/e: 737.7 (M+H)1, 2.22 min (method 1).

Aufarbeitung

  1. customflushed with nitrogen
  2. customsealed
  3. temperatureAfter heating the mixture for 22 h
  4. temperatureit was cooled to rt
  5. additiondiluted with water (5 mL)
  6. extractionextracted with dichloromethane (3×5 mL)
  7. dry with materialThe organic layers were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was used in the next step with no additional purification
  11. custom737.7 (M+H)1, 2.22 min (method 1)

Quellen und Nachweise

ORD-Eintrag
ord-e0ea9513bcd1460ca5778d143be87c28
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249180B2

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