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Phosphoric Acid → ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-hydroxyethyl)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)cyclohex-3-enecarboxylate

HRID 1400995
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400995
[NH2:1][C@:2]12[CH2:38][CH2:37][C@@H:36]([C:39]([CH3:41])=[CH2:40])[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([CH3:35])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1.[CH2:42](Br)[CH2:43][OH:44].[I-].[K+].P(=O)(O)(O)O.[K]>C(#N)C>[OH:44][CH2:43][CH2:42][NH:1][C@:2]12[CH2:38][CH2:37][C@@H:36]([C:39]([CH3:41])=[CH2:40])[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([CH3:35])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C:11]([C:24]2[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH:25]=2)=[CH:10][CH2:9]3)[CH2:6][CH2:5]1
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Komponenten

7

Edukt 5

HCID 1004Phosphoric AcidHCID 4875Potassium IodideHCID 108982-BromoethanolHCID 5462222PotassiumHCID 86692333ethyl 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)cyclohex-3-enecarboxylate

Produkt 1

HCID 86692352ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-hydroxyethyl)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)cyclohex-3-enecarboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a sealable vial was added 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)cyclohex-3-enecarboxylate (0.156 g, 0.278 mmol), ethylene bromohydrin (0.059 mL, 0.833 mmol), potassium iodide (0.138 g, 0.833 mmol), and phosphoric acid, potassium salt (0.295 g, 1.388 mmol). The mixture was diluted with acetonitrile (2 mL), was flushed with nitrogen, then was sealed and heated to 100° C. After 15 h of heating, the mixture was cooled to rt. LC/MS still showed starting material present, so an additional 0.059 mL of ethylene bromohydrin was added, the mixture was diluted with 1 mL of acetonitrile, and it was sealed and heated to 120° C. After heating the mixture for an additional 20 h, it was cooled to rt, and diluted with 10 mL of water. The solids that formed were collected by filtration and were washed with water to give ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-hydroxyethyl)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)cyclohex-3-enecarboxylate (0.145 g, 0.239 mmol, 86% yield) as an off-white solid. LCMS: m/e 606.7 (M+H)+, 2.18 min (method 1).

Aufarbeitung

  1. customwas flushed with nitrogen
  2. customwas sealed
  3. temperatureAfter 15 h of heating
  4. temperaturethe mixture was cooled to rt
  5. additionso an additional 0.059 mL of ethylene bromohydrin was added
  6. additionthe mixture was diluted with 1 mL of acetonitrile, and it
  7. customwas sealed
  8. temperatureheated to 120° C
  9. temperatureAfter heating the mixture for an additional 20 h
  10. temperatureit was cooled to rt
  11. additiondiluted with 10 mL of water
  12. customThe solids that formed
  13. filtrationwere collected by filtration
  14. washwere washed with water

Quellen und Nachweise

ORD-Eintrag
ord-835d9c578bc84153a9278ae6d2521a79
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906889B2

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