3-(4-((1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-3a-(benzyloxycarbonyl)-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)phenyl)propanoic acid → (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-(2-carboxyethyl)phenyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

HRID 406865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406865
C([O:8][C:9]([C@:11]12[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:12]1[C@@H:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[CH:16]([C@:17]3([CH3:44])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:35][CH:34]=2)=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:41]([CH2:40][CH2:39][C:36]1[CH:37]=[CH:38][C:33]([C:20]2[C:21]([CH3:32])([CH3:31])[C@H:22]3[C@:17]([CH3:44])([CH2:18][CH:19]=2)[C@@H:16]2[C@:25]([CH3:30])([C@@:26]4([CH3:29])[C@H:13]([CH2:14][CH2:15]2)[C@H:12]2[C@H:45]([C:48]([CH3:50])=[CH2:49])[CH2:46][CH2:47][C@:11]2([C:9]([OH:10])=[O:8])[CH2:28][CH2:27]4)[CH2:24][CH2:23]3)=[CH:34][CH:35]=1)([OH:43])=[O:42]

Komponenten

4

Edukt 1

HCID 677773223-(4-((1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-3a-(benzyloxycarbonyl)-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)phenyl)propanoic acid

Produkt 1

HCID 54761941(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-(2-carboxyethyl)phenyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-(4-((1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-3a-(benzyloxycarbonyl)-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)phenyl)propanoic acid (60 mg, 0.089 mmol) and 10% Pd/C (28.3 mg, 0.027 mmol) in Ethyl acetate (2 mL) was stirred under 1 ATM of H2 for 24 hours. LCMS indicated the completion of the reaction. The reaction mixture was filtered and the white solid was collected. The solid was purified by Prep. HPLC to provide the desired product, (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(2-carboxyethyl)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]chrysene-3a-carboxylic acid, as white solid (10.32 mg, 30%). LCMS: m/e 585.59 (M−H)−, 4.38 min (method 2). 1H NMR (599 MHz, DMSO-D6_CDCl3) δ ppm 0.91 (s, 3H), 0.93 (s, 3H), 1.00 (s, 6H), 1.02 (s, 3H), 1.05-1.72 (m, 17H), 1.71 (s, 3H), 1.84-1.95 (m, 2H), 2.10 (dd, J=17.58, 6.44 Hz, 1H), 2.20 (d, J=11.72 Hz, 1H), 2.30-2.39 (m, 1H), 2.60 (s, 2H), 2.85 (t, J=7.62 Hz, 2H), 3.02 (td, J=10.25, 5.27 Hz, 1H), 4.61 (br. s, 1H), 4.74 (s, 1H), 5.23 (d, J=5.27 Hz, 1H), 6.94 (d, J=7.62 Hz, 1H), 6.98 (s, 1H), 7.12 (d, J=8.20 Hz, 1H), 7.20 (t, J=7.62 Hz, 1H).

Aufarbeitung

  1. customthe completion of the reaction
  2. filtrationThe reaction mixture was filtered
  3. customthe white solid was collected
  4. customThe solid was purified by Prep

Quellen und Nachweise

ORD-Eintrag
ord-0626634343cf47f1972c3bd5dea7806a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754068B2

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