Water → HCID 71597671, compound

HRID 405076Notes

Reaction equation

HRID 405076 reaction equation
C[O:2][C:3]([C:5]1[CH:52]=[CH:51][C:8]([CH2:9][CH2:10][NH:11][CH2:12][C@:13]23[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:14]2[C@@H:15]2[C@@:28]([CH3:31])([CH2:29][CH2:30]3)[C@@:27]3([CH3:32])[C@@H:18]([C@:19]4([CH3:44])[C@@H:24]([CH2:25][CH2:26]3)[C:23]([CH3:34])([CH3:33])[C:22]([C:35]3[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=3)=[CH:21][CH2:20]4)[CH2:17][CH2:16]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Li+].O>O1CCOCC1.CO>[C:3]([C:5]1[CH:52]=[CH:51][C:8]([CH2:9][CH2:10][NH:11][CH2:12][C@:13]23[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:14]2[C@@H:15]2[C@@:28]([CH3:31])([CH2:29][CH2:30]3)[C@@:27]3([CH3:32])[C@@H:18]([C@:19]4([CH3:44])[C@@H:24]([CH2:25][CH2:26]3)[C:23]([CH3:34])([CH3:33])[C:22]([C:35]3[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=3)=[CH:21][CH2:20]4)[CH2:17][CH2:16]2)=[CH:7][CH:6]=1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 71597820HCID 71597820, compound

Product 1

HCID 71597671HCID 71597671, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((4-(methoxycarbonyl)phenethylamino)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 (5 mg) in dioxane (2 ml) and MeOH (2 ml), 3 mg of lithium hydroxide was added followed by 0.5 ml of water. The resulting clear solution was stirred at 50° C. for 12 h. The solvent was removed in vacuo and yellow solid was obtained. The crude material was purified by prep. HPLC to afford the title compound as a white solid (1.1 mg, 22.0%). LCMS: m/e 692.5 (MH+), 2.28 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 6.50 (d, J=8.3 Hz, 2H), 6.38 (d, J=8.3 Hz, 2H), 5.91 (d, J=8.3 Hz, 2H), 5.68 (d, J=8.3 Hz, 2H), 3.75-3.81 (m, 1H), 3.22 (s, 1H), 3.11 (s, 1H), 1.79-1.91 (m, 2H), 1.66-1.75 (m, 1H), 1.51-1.66 (m, 2H), 1.33 (s, 1H), 0.84-1.02 (m, 1H), 0.44-0.68 (m, 2H), 0.10-0.33 (m, 8H), 0.12-0.10 (m, 6H), 0.34-0.12 (m, 6H), 0.42-0.34 (m, 6H), 0.46 (s, 3H), 0.49 (s, 3H), 0.57 (s, 3H), 0.59 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customyellow solid was obtained
  3. customThe crude material was purified by prep

Sources & evidence

ORD record
ord-88b92f7611ac431d80f3b6f7133ae8e0
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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