Sodium Hydroxide → 4-((((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)phenyl)-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-3a-yl)methyl)(2-(dimethylamino)ethyl)amino)-4-oxobutanoic acid

HRID 405073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405073
[CH3:1][N:2]([CH3:57])[CH2:3][CH2:4][N:5]([CH2:14][C@:15]12[CH2:53][CH2:52][C@@H:51]([C:54]([CH3:56])=[CH2:55])[C@@H:16]1[C@@H:17]1[C@@:30]([CH3:33])([CH2:31][CH2:32]2)[C@@:29]2([CH3:34])[C@@H:20]([C@:21]3([CH3:50])[C@@H:26]([CH2:27][CH2:28]2)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]2[CH:49]=[CH:48][C:40]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:39][CH:38]=2)=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)[C:6](=[O:13])[CH2:7][CH2:8][C:9]([O:11]C)=[O:10].[OH-].[Na+]>O1CCOCC1>[C:44]([O:43][C:41]([C:40]1[CH:48]=[CH:49][C:37]([C:24]2[C:25]([CH3:36])([CH3:35])[C@H:26]3[C@:21]([CH3:50])([CH2:22][CH:23]=2)[C@@H:20]2[C@:29]([CH3:34])([C@@:30]4([CH3:33])[C@H:17]([CH2:18][CH2:19]2)[C@H:16]2[C@H:51]([C:54]([CH3:56])=[CH2:55])[CH2:52][CH2:53][C@:15]2([CH2:14][N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:57])[C:6](=[O:13])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:32][CH2:31]4)[CH2:28][CH2:27]3)=[CH:38][CH:39]=1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86676411tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((N-(2-(dimethylamino)ethyl)-4-methoxy-4-oxobutanamido)methyl)-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)benzoate

Produkt 1

HCID 866764104-((((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)phenyl)-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-3a-yl)methyl)(2-(dimethylamino)ethyl)amino)-4-oxobutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((N-(2-(dimethylamino)ethyl)-4-methoxy-4-oxobutanamido)methyl)-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)benzoate (53 mg, 0.068 mmol) in 1,4-dioxane (1 ml) was added NaOH (0.338 ml, 0.338 mmol). The mixture was heated to 75° C. for 3 h. The mixture was cooled to rt and was quenched with 1N HCl (3 ml) and extracted with dichloromethane (3×7 ml). The combined organic layers were dried with Na2SO4, were filtered, and concentrated under reduced pressure. The crude product was used in the next step with no additional purification. LCMS: m/e 771.6 (M+H)+, 2.70 min (method 6).

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. customwas quenched with 1N HCl (3 ml)
  3. extractionextracted with dichloromethane (3×7 ml)
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. filtrationwere filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was used in the next step with no additional purification
  8. customm/e 771.6 (M+H)+, 2.70 min (method 6)

Quellen und Nachweise

ORD-Eintrag
ord-2dfa880277c84b55a6a6f93d997e983a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748415B2

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