HCID 67777449, compound → HCID 67776938, compound

HRID 406861Notes

Reaction equation

HRID 406861 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]([CH3:41])([CH3:40])[C@H:12]3[C@:25]([CH3:28])([CH2:26][CH:27]=2)[CH:24]2[C@:15]([CH3:39])([C@@:16]4([CH3:38])[C@H:21]([CH2:22][CH2:23]2)[C@H:20]2[C@H:29]([C:32]([CH3:34])=[CH2:33])[CH2:30][CH2:31][C@:19]2([C:35]([OH:37])=[O:36])[CH2:18][CH2:17]4)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]>CCOC(C)=O.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([C@H:10]2[CH2:27][CH2:26][C@@:25]3([CH3:28])[C@@H:12]([CH2:13][CH2:14][C@:15]4([CH3:39])[CH:24]3[CH2:23][CH2:22][C@H:21]3[C@@:16]4([CH3:38])[CH2:17][CH2:18][C@@:19]4([C:35]([OH:37])=[O:36])[CH2:31][CH2:30][CH:29]([CH:32]([CH3:34])[CH3:33])[C@@H:20]43)[C:11]2([CH3:41])[CH3:40])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 67777449HCID 67777449, compound

Product 1

HCID 67776938HCID 67776938, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-9-(3-carboxyphenyl)-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 (20 mg, 0.036 mmol) in EtOAc (3 mL) was added 10% Pd/C (4 mg, 0.0036 mmol). The reaction mixture was stirred at room temperature under 1 ATM of H2 for 36 h. LCMS indicated the reaction was complete and the desired product was formed. The reaction mixture was filtered through a celite pad which was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to provide (3aS,5aR,5bR,7aS,9S,11aS,13aR,13bR)-9-(3-carboxyphenyl)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid as a white solid (8 mg, 38%). LCMS: m/e 561.45 (M−H)−, 3.53 min (method 5). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.64 (s, 3H), 0.71 (s, 3H), 0.74 (d, J=6.71 Hz, 3H), 0.80-0.86 (m, 3H), 0.92 (s, 3H), 0.93 (s, 3H), 0.95-0.98 (m, 3H), 0.98-1.66 (m, 18H), 1.68-1.82 (m, 3H), 2.07-2.22 (m, 3H), 2.23-2.34 (m, 1H), 2.42 (dd, J=13.12, 2.75 Hz, 1H), 7.36 (t, J=7.48 Hz, 1H), 7.39-7.46 (m, 1H), 7.70-7.80 (m, 2H).

Sources & evidence

ORD record
ord-52bc50b21beb4c10b7504e61bbed08d0
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

Loading…