Sodium Hydroxide → HCID 71597764, compound

HRID 405093Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-(2-ethoxy-2-oxoethyl)ureido)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 (7 mg, 10.40 mmol) was dissolved in dioxane (2 ml). Sodium hydroxide solution, 1N (0.021 ml, 0.021 mmol) was added. The mixture was stirred at 70° C. for 2 h. The solvent was evaporated and the residue was purified by prep. HPLC to afford the title compound as a white solid (4 mg, 32.8%). LCMS: m/e 645.3 (MH+), 2.58 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.90 (m, J=8.3 Hz, 2H), 7.20 (m, J=8.3 Hz, 2H), 5.21-5.36 (m, 1H), 4.70 (d, J=1.8 Hz, 1H), 4.57 (s, 1H), 3.83 (s, 2H), 3.44 (d, J=13.8 Hz, 1H), 2.95 (d, J=13.6 Hz, 1H), 2.38-2.60 (m, 1H), 2.13 (dd, J=17.1, 6.5 Hz, 1H), 1.93-2.08 (m, 1H), 1.76-1.93 (m, 2H), 1.60-1.76 (m, 8H), 1.40-1.60 (m, 6H), 1.35-1.40 (m, 1H), 1.29-1.35 (m, 1H), 1.18-1.29 (m, 3H), 1.16 (s, 3H), 1.05-1.13 (m, 2H), 1.03 (s, 3H), 1.02 (s, 3H), 0.97 (s, 3H), 0.92 (s, 3H).

Workup

customThe solvent was evaporated
customthe residue was purified by prep

Sources & evidence

ORD record: ord-070648efc86042c69ffbf0c020c075b0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748415B2

Reaction notes

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