Sodium Hydroxide → HCID 68358153, compound

HRID 85719Notes

Reaction equation

HRID 85719 reaction equation
C[O:2][C:3](=[O:46])[CH2:4][CH2:5][NH:6][C@:7]12[CH2:42][CH2:41][C@@H:40]([C:43]([CH3:45])=[CH2:44])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:39])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1.[OH-].[Na+]>O1CCOCC1>[C:3]([CH2:4][CH2:5][NH:6][C@:7]12[CH2:42][CH2:41][C@@H:40]([C:43]([CH3:45])=[CH2:44])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:39])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:30]=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:37][CH:38]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([OH:46])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86676634methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-methoxy-3-oxopropyl)amino)-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

Product 1

HCID 68358153HCID 68358153, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-methoxy-3-oxopropyl)amino)-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 (15 mg, 0.024 mmol) and sodium hydroxide (0.238 mL, 0.238 mmol) in dioxane (1 mL) was heated up at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and then filtered, the clear solution was purified by HPLC to provide the title compound as a white solid (5 mg, 33%). LCMS: m/e 602.43 (M+H)+, 2.25 min (method 10). 1H NMR (500 MHz, Acetic) δ 8.04 (d, J=8.2 Hz, 2H), 7.30 (d, J=8.2 Hz, 2H), 5.37 (d, J=4.9 Hz, 1H), 4.86 (s, 1H), 4.74 (s, 1H), 3.39 (t, J=4.4 Hz, 2H), 3.17-3.02 (m, 1H), 2.98-2.80 (m, 2H), 2.31-1.02 (m, 22H), 1.77 (s, 3H), 1.24 (s, 3H), 1.14 (s, 3H), 1.09 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe clear solution was purified by HPLC

Sources & evidence

ORD record
ord-2af3bf5b51404b5ea01c4b552b718330
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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