Sodium Hydroxide → HCID 54764621, compound

HRID 2405486Notes

Reaction equation

HRID 2405486 reaction equation
[CH3:1][N:2]([CH3:52])[CH2:3][CH2:4][N:5]([CH2:49][CH2:50][OH:51])[C:6]([C@:8]12[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:42])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:41]=[CH:40][C:33]([C:34]([O:36]CCO)=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7].[OH-].[Na+]>O1CCOCC1.O>[CH3:52][N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH2:49][CH2:50][OH:51])[C:6]([C@:8]12[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:42])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:41]=[CH:40][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67776024HCID 67776024, compound

Product 1

HCID 54764621HCID 54764621, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of 2-hydroxyethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(dimethylamino)ethyl)(2-hydroxyethyl)carbamoyl)-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)benzoate (6 mg, 8.37 μmol) and sodium hydroxide (0.042 mL, 0.042 mmol) in dioxane (1 mL) was heated up at 78° C. for 3 hours. The solution was diluted with water and filtered. The clear solution was purified by prep HPLC to provide the title compound as a white solid (5 mg, 84%). LCMS: m/e 673.58 (M+H)+, 2.08 min (method 1). 1H NMR (500 MHz, Acetic Acid-d4) δ ppm 8.03 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.55 Hz, 2H), 5.43-5.31 (m, 1H), 4.78 (d, J=1.53 Hz, 1H), 4.66 (s, 1H), 4.26-4.13 (m, 2H), 3.90-3.78 (m, 2H), 3.75-3.63 (m, 4H), 3.30 (s, 6H), 3.20-3.07 (m, 1H), 2.60-2.45 (m, 1H), 1.74 (s, 3H), 2.26-1.22 (m, 21H), 1.08 (s, 3H), 1.07 (s, 3H), 1.05 (s, 3H), 1.01 (s, 3H), 0.99 (s, 3H).

Workup

  1. filtrationfiltered
  2. customThe clear solution was purified by prep HPLC

Sources & evidence

ORD record
ord-295942fc402a422dbf8c907e12bdeda5
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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