Sodium Hydroxide → 5-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-dimethylaminoethylcarbamoyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]thiophene-2-carboxylic acid

HRID 2405484Notes

Reaction equation

HRID 2405484 reaction equation
[CH3:1][N:2]([CH3:46])[CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:42][CH2:41][C@@H:40]([C:43]([CH3:45])=[CH2:44])[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([CH3:39])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[S:34][C:33]([C:35]([O:37]C)=[O:36])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7].[OH-].[Na+]>O1CCOCC1>[CH3:46][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:42][CH2:41][C@@H:40]([C:43]([CH3:45])=[CH2:44])[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([CH3:39])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[S:34][C:33]([C:35]([OH:37])=[O:36])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67775008HCID 67775008, compound

Product 1

HCID 547643555-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-dimethylaminoethylcarbamoyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 5-((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)thiophene-2-carboxylate (60 mg, 0.092 mmol) and sodium hydroxide (0.028 mL, 0.277 mmol) in dioxane (2 mL) was heated up at 70° C. for 3 hours. LCMS indicated the formation of desired product. The reaction mixture was filtered and purified by prep HPLC to give the title compound as a white solid (6.4 mg, 10%). LCMS: m/e 635.35 (M+H)+, 2.18 min (method 1). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.49 (t, J=5.65 Hz, 1H), 7.37 (br. s., 1H), 6.86 (d, J=3.66 Hz, 1H), 5.72 (d, J=4.88 Hz, 1H), 4.67 (d, J=2.44 Hz, 1H), 4.55 (s, 1H), 3.21 (td, J=13.20, 6.56 Hz, 1H), 3.08-2.98 (m, 2H), 2.61-2.53 (m, 1H), 2.26 (td, J=6.79, 2.29 Hz, 2H), 2.15 (s, 6H), 2.15-2.06 (m, 2H), 1.64 (s, 3H), 1.82-1.04 (m, 19H), 1.03 (s, 3H), 1.01 (s, 3H), 0.94 (s, 3H), 0.91 (s, 3H), 0.87 (s, 3H).

Sources & evidence

ORD record
ord-dd561008656342d081b08dd7aedac2eb
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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