Water → HCID 71597899, compound

HRID 405086Notes

Reaction equation

HRID 405086 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:54])[CH2:13][NH:14][CH2:15][C@:16]23[CH2:50][CH2:49][C@@H:48]([C:51]([CH3:53])=[CH2:52])[C@@H:17]2[C@@H:18]2[C@@:31]([CH3:34])([CH2:32][CH2:33]3)[C@@:30]3([CH3:35])[C@@H:21]([C@:22]4([CH3:47])[C@@H:27]([CH2:28][CH2:29]3)[C:26]([CH3:37])([CH3:36])[C:25]([C:38]3[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=3)=[CH:24][CH2:23]4)[CH2:20][CH2:19]2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].O>CO.O1CCOCC1>[C:42]([C:41]1[CH:45]=[CH:46][C:38]([C:25]2[C:26]([CH3:37])([CH3:36])[C@H:27]3[C@:22]([CH3:47])([CH2:23][CH:24]=2)[C@@H:21]2[C@:30]([CH3:35])([C@@:31]4([CH3:34])[C@H:18]([CH2:19][CH2:20]2)[C@H:17]2[C@H:48]([C:51]([CH3:53])=[CH2:52])[CH2:49][CH2:50][C@:16]2([CH2:15][NH:14][CH2:13][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[O:54])[CH2:33][CH2:32]4)[CH2:29][CH2:28]3)=[CH:39][CH:40]=1)([OH:44])=[O:43]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 71597898HCID 71597898, compound

Product 1

HCID 71597899HCID 71597899, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

The title compound was prepared following the procedure described below: To the solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-(ethoxycarbonyl)piperidin-1-yl)-2-oxoethylamino)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 (12 mg, 0.016 mmol) in MeOH (3.00 ml) and dioxane (3 ml), sodium hydroxide (10 mg, 0.250 mmol) was added followed by 0.5 ml of water. The resulting suspension was stirred at 25° C. for 4 h. The solvent was removed in vacuo, the product was isolated by prep. HPLC as a white solid (5 mg, 41.4%). LCMS: m/e 713.5 (MH+), 2.37 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.95 (m, 2H), 7.27 (m, 2H), 5.32 (d, J=4.5 Hz, 1H), 4.76 (d, J=1.8 Hz, 1H), 4.66 (s, 1H), 4.29-4.46 (m, 1H), 4.09-4.25 (m, 2H), 3.64-3.85 (m, 1H), 3.17-3.32 (m, 2H), 3.05 (m, 1H), 2.87 (dd, J=12.8, 4.8 Hz, 1H), 2.67 (tt, J=10.8, 4.0 Hz, 1H), 2.49 (dt, J=10.9, 5.5 Hz, 1H), 2.07-2.29 (m, 2H), 1.85-2.07 (m, 4H), 1.67-1.85 (m, 8H), 1.43-1.67 (m, 9H), 1.36 (br. s., 2H), 1.32 (d, J=6.5 Hz, 2H), 1.24 (d, J=14.8 Hz, 1H), 1.13-1.20 (m, 4H), 1.11 (s, 3H), 1.04 (s, 3H), 0.99 (s, 3H), 0.98 (s, 3H).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customthe product was isolated by prep
  4. customm/e 713.5 (MH+), 2.37 min (method 3)

Sources & evidence

ORD record
ord-acecb73c19964edfa806a86a462f5206
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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