Hydrochloric Acid → HCID 71596697, compound

HRID 405085Notes

Reaction equation

HRID 405085 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:55])[CH2:13][CH2:14][NH:15][CH2:16][C@:17]23[CH2:51][CH2:50][C@@H:49]([C:52]([CH3:54])=[CH2:53])[C@@H:18]2[C@@H:19]2[C@@:32]([CH3:35])([CH2:33][CH2:34]3)[C@@:31]3([CH3:36])[C@@H:22]([C@:23]4([CH3:48])[C@@H:28]([CH2:29][CH2:30]3)[C:27]([CH3:38])([CH3:37])[C:26]([C:39]3[CH:47]=[CH:46][C:42]([C:43]([OH:45])=[O:44])=[CH:41][CH:40]=3)=[CH:25][CH2:24]4)[CH2:21][CH2:20]2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].O.Cl>O1CCOCC1.CO>[C:43]([C:42]1[CH:46]=[CH:47][C:39]([C:26]2[C:27]([CH3:38])([CH3:37])[C@H:28]3[C@:23]([CH3:48])([CH2:24][CH:25]=2)[C@@H:22]2[C@:31]([CH3:36])([C@@:32]4([CH3:35])[C@H:19]([CH2:20][CH2:21]2)[C@H:18]2[C@H:49]([C:52]([CH3:54])=[CH2:53])[CH2:50][CH2:51][C@:17]2([CH2:16][NH:15][CH2:14][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:55])[CH2:34][CH2:33]4)[CH2:30][CH2:29]3)=[CH:40][CH:41]=1)([OH:45])=[O:44]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 71597552HCID 71597552, compound

Product 1

HCID 71596697HCID 71596697, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-(4-(ethoxycarbonyl)piperidin-1-yl)-3-oxopropylamino)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 (16 mg, 0.021 mmol) in dioxane (1 ml) and methanol (2 ml) was added 1N sodium hydroxide (0.3 ml, 0.1 mmol) and H2O (0.5 ml). The resulting mixture was stirred at rt for 10 days. The reaction mixture was neutralized with 1N HCl and concentrated in vacuo. The crude product was purified by prep. HPLC to afford the title compound (8 mg). MS: m/e 727.6 (MH+), 1.69 min (method 2). 1H NMR (400 MHz, MeOD) δ ppm 0.95 (s, 3H) 0.97 (s, 3H) 1.04 (s, 3H) 1.08 (s, 3H) 1.17 (d, J=2.76 Hz, 3H) 1.73 (s, 3H) 0.87-1.86 (m, 23H) 1.92-2.10 (m, 3H) 2.15 (dd, J=17.32, 6.53 Hz, 1H) 2.47-2.56 (m, 1H) 2.57-2.67 (m, J=7.34, 7.12, 7.12, 3.76 Hz, 1H) 2.83-2.94 (m, 4H) 3.16-3.41 (m, 4H) 3.82-3.91 (m, 1H) 4.35-4.44 (m, 1H) 4.64 (s, 1H) 4.76 (d, J=1.51 Hz, 1H) 5.30 (d, J=5.27 Hz, 1H) 7.22 (d, J=8.28 Hz, 2H) 7.91 (d, J=8.28 Hz, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-a9083d2af2104181b513b20209b2be09
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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