Sodium Hydroxide → HCID 60152239, compound

HRID 85638Notes

Reaction equation

HRID 85638 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C@:5]12[CH2:40][CH2:39][C@@H:38]([C:41]([CH3:43])=[CH2:42])[C@@H:6]1[C@@H:7]1[C@@:20]([CH3:23])([CH2:21][CH2:22]2)[C@@:19]2([CH3:24])[C@@H:10]([C@:11]3([CH3:37])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:26])([CH3:25])[C:14]([C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1.[OH-].[Na+]>O1CCOCC1.CO>[OH:1][CH2:2][CH2:3][NH:4][C@:5]12[CH2:40][CH2:39][C@@H:38]([C:41]([CH3:43])=[CH2:42])[C@@H:6]1[C@@H:7]1[C@@:20]([CH3:23])([CH2:21][CH2:22]2)[C@@:19]2([CH3:24])[C@@H:10]([C@:11]3([CH3:37])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:26])([CH3:25])[C:14]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:35][CH:36]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86676600methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-hydroxyethyl)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 60152239HCID 60152239, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-hydroxyethylamino)-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 (35 mg, 0.060 mmol) in dioxane (1 mL) was added NaOH (1N) (0.298 mL, 0.298 mmol). The mixture was heated to 85° C. for 15 h then was cooled to rt. The mixture was diluted with MeOH and was purified by prep HPLC. The fractions containing the expected product were combined and concentrated under reduced pressure to give the title compound (25 mg, 0.041 mmol, 69.5% yield) as a white solid. LCMS: m/e 574.5 (M+H)+, 1.69 min (method 2). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (2H, d, J=8.2 Hz), 7.30 (2H, d, J=8.2 Hz), 5.37 (1H, d, J=4.6 Hz), 4.86 (1H, s), 4.75 (1H, s), 3.95-4.11 (2H, m), 3.25-3.43 (2H, m), 2.90-2.98 (1H, m), 1.77 (3H, s), 1.21 (3H, s), 1.14 (3H, s), 1.09 (3H, s), 1.02 (3H, s), 1.00 (3H, s), 0.97-2.32 (22H, m).

Workup

  1. temperaturethen was cooled to rt
  2. customwas purified by prep HPLC
  3. additionThe fractions containing the expected product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-373060f0e93547f3b81aab46064339a6
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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