HCID 86678456, compound → HCID 86678455, compound

HRID 405707Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 4-(((1R,3aS,5aR,5bR,7aR,9S,11aR,13aR,13bR)-3a-((2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (10 mg, 0.014 mmol) and 10% palladium on carbon (14.84 mg, 0.014 mmol) in methanol (5 mL) was stirred at 20° C. for 18 h under hydrogen at 40 psi. The reaction mixture was filtered to remove the catalyst and the solution was purified by reverse phase prep HPLC to provide the title compound as a white solid (4.1 mg, 39%). LCMS: m/e 719.53 (M+H)+, 2.41 min (method 1). 1H NMR (500 MHz, Acetic) δ 4.58 (dd, J=10.5, 5.6 Hz, 1H), 3.43-3.36 (m, 1H), 3.34-3.19 (m, 6H), 3.18-3.01 (m, 5H), 2.80-2.61 (m, 2H), 2.27-0.89 (m, 26H), 1.33 (s, 3H), 1.32 (s, 3H), 1.23 (s, 3H), 1.09 (s, 3H), 0.98 (s, 3H), 0.93 (d, J=6.7 Hz, 3H), 0.90 (s, 6H), 0.84 (d, J=6.7 Hz, 3H).

Workup

filtrationThe reaction mixture was filtered
customto remove the catalyst
customthe solution was purified by reverse phase prep HPLC

Sources & evidence

ORD record: ord-d5f58fe9794349e6a7478a7db16deac7
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754069B2

Reaction notes

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