Sodium Hydroxide → HCID 71597794, compound

HRID 405094Notes

Reaction equation

HRID 405094 reaction equation
[CH2:1]([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.CO>[CH3:1][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: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

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71597858HCID 71597858, compound

Product 1

HCID 71597794HCID 71597794, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

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) and methanol (1 ml). A solution of sodium hydroxide (1N, 0.021 ml, 0.021 mmol) was added. The mixture was stirred at 70° C. for 2 h. The solvent was removed under reduced pressure and the residue was purified by prep. HPLC to afford the title compound as a white solid (2 mg, 29.2%). LCMS: m/e 659.4 (MH+), 2.84 min (method 3). 1H NMR (500 MHz, MeOD) δ ppm 7.86 (d, J=8.2 Hz, 2H), 7.14 (d, J=7.9 Hz, 2H), 5.23-5.38 (m, 1H), 4.74 (s, 1H), 4.62 (s, 1H), 3.91 (s, 2H), 3.71-3.78 (m, 3H), 2.95-3.10 (m, 1H), 2.46-2.62 (m, 1H), 2.12-2.25 (m, 1H), 2.05 (s, 1H), 1.99-2.03 (m, 1H), 1.91-1.99 (m, 6H), 1.89 (br. s., 2H), 1.76-1.83 (m, 2H), 1.71-1.76 (m, 4H), 1.69 (br. s., 1H), 1.48 (br. s., 4H), 1.31 (br. s., 4H), 1.19 (s, 3H), 1.07 (br. s., 3H), 1.05 (s, 3H), 0.97 (s, 3H), 0.96 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-62f8dce6688141038edbd01061abd250
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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