Trifluoroacetic acid → 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-dimethylaminoethyl-(4-hydroxy-4-oxo-butanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

HRID 405074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405074
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([CH3:56])([CH3:55])[C@H:16]3[C@:29]([CH3:32])([CH2:30][CH:31]=2)[C@@H:28]2[C@:19]([CH3:54])([C@@:20]4([CH3:53])[C@H:25]([CH2:26][CH2:27]2)[C@H:24]2[C@H:33]([C:36]([CH3:38])=[CH2:37])[CH2:34][CH2:35][C@:23]2([CH2:39][N:40]([CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])[C:41](=[O:47])[CH2:42][CH2:43][C:44]([OH:46])=[O:45])[CH2:22][CH2:21]4)[CH2:18][CH2:17]3)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:44]([CH2:43][CH2:42][C:41]([N:40]([CH2:39][C@:23]12[CH2:35][CH2:34][C@@H:33]([C:36]([CH3:38])=[CH2:37])[C@@H:24]1[C@@H:25]1[C@@:20]([CH3:53])([CH2:21][CH2:22]2)[C@@:19]2([CH3:54])[C@@H:28]([C@:29]3([CH3:32])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:56])([CH3:55])[C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:13][CH:12]=2)=[CH:31][CH2:30]3)[CH2:27][CH2:26]1)[CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])=[O:47])([OH:46])=[O:45]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 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

Produkt 1

HCID 715963744-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-dimethylaminoethyl-(4-hydroxy-4-oxo-butanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acidAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 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 (47 mg, 0.061 mmol) in DCM (1 ml) was added TFA (0.25 ml, 3.24 mmol). The mixture was stirred at rt. After 1.75 h, The mixture was concentrated under reduced pressure, was diluted with dioxane and MeOH and was purified by prep HPLC to afford 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-carboxy-N-(2-(dimethylamino)ethyl)propanamido)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)benzoic acid as a white solid (25 mg, 0.035 mmol, 57.4% yield. LCMS: m/e 715.4 (M+H)+, 2.16 min (method 6).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionwas diluted with dioxane and MeOH
  3. customwas purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4c197e93399c45cf81163c3c8904cba2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748415B2

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