HCID 67775804, compound → HCID 67776346, compound

HRID 2405487Notes

Reaction equation

HRID 2405487 reaction equation
[CH3:1][N:2]([CH3:47])[CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[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([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7]>C(O)(=O)C.CO.[Pd]>[CH3:47][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:43][CH2:42][C@@H:41]([CH:44]([CH3:45])[CH3:46])[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([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:28])([CH3:29])[C:17]([C:30]2[CH:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7]

Participants

5

Reactant 1

HCID 67775804HCID 67775804, compound

Product 1

HCID 67776346HCID 67776346, compoundYield 22.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-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 (27 mg, 0.042 mmol) and Pd/C (14.30 mg, 0.013 mmol) in acetic acid (4 mL) and MeOH (4 mL) was reacted in Parr shaker for 18 hours under 40 psi. The reaction mixture was filtered through celite to remove Pd/C. The filtrates were concentrated under reduced pressure. The residue was dissolved in methanol and then purified by prep HPLC to provide the title compound as a white solid (6 mg, 22%). LCMS: m/e 645.62 (M+H)+, 2.87 min (method 1). 1H NMR (500 MHz, Acetic Acid-d4) δ ppm 7.98 (d, J=8.24 Hz, 2H), 7.27 (d, J=8.24 Hz, 2H), 5.37 (d, J=4.88 Hz, 1H), 3.94 (s, 3H), 3.74 (t, J=5.95 Hz, 2H), 3.43-3.32 (m, 2H), 2.95 (s, 6H), 2.59-2.48 (m, 1H), 2.42-2.31 (m, 1H), 2.28-1.10 (m, 22H), 1.07 (d, J=3.97 Hz, 6H), 1.05 (s, 3H), 1.00 (s, 3H), 0.99 (s, 3H), 0.91 (d, J=6.71 Hz, 3H), 0.82 (d, J=6.71 Hz, 3H).

Workup

  1. customwas reacted in Parr shaker for 18 hours under 40 psi
  2. filtrationThe reaction mixture was filtered through celite
  3. customto remove Pd/C
  4. concentrationThe filtrates were concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol
  6. custompurified by prep HPLC

Sources & evidence

ORD record
ord-2de0bdff07b94b70b71e3c69d64a8610
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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