Sodium Hydroxide → HCID 86676590, compound

HRID 85628Notes

Reaction equation

HRID 85628 reaction equation
C[C:2]1[CH:10]=[C:9]([C:11]2[C:12]([CH3:51])([CH3:50])[C@H:13]3[C@:26]([CH3:29])([CH2:27][CH:28]=2)[C@@H:25]2[C@:16]([CH3:49])([C@@:17]4([CH3:48])[C@H:22]([CH2:23][CH2:24]2)[C@H:21]2[C@H:30]([C:33]([CH3:35])=[CH2:34])[CH2:31][CH2:32][C@:20]2([NH:36][CH2:37][CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][S:43](=[O:47])(=[O:46])[CH2:42][CH2:41]2)[CH2:19][CH2:18]4)[CH2:15][CH2:14]3)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+]>O1CCOCC1>[O:47]=[S:43]1(=[O:46])[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][CH2:37][NH:36][C@:20]23[CH2:32][CH2:31][C@@H:30]([C:33]([CH3:35])=[CH2:34])[C@@H:21]2[C@@H:22]2[C@@:17]([CH3:48])([CH2:18][CH2:19]3)[C@@:16]3([CH3:49])[C@@H:25]([C@:26]4([CH3:29])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:51])([CH3:50])[C:11]([C:9]3[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[CH:2][CH:10]=3)=[CH:28][CH2:27]4)[CH2:24][CH2:23]2)[CH2:41][CH2:42]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86676592methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-(1,1-dioxido-4-thiomorpholinyl)propyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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)benzoic acid

Product 1

HCID 86676590HCID 86676590, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-(1,1-dioxido-4-thiomorpholinyl)propyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-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)benzoic acid (15 mg, 0.021 mmol) and 1N sodium hydroxide (0.104 mL, 0.104 mmol) in dioxane (1 mL) was heated at 78° C. for 3 hours. The reaction mixture was purified by prep HPLC to provide the title compound as a white solid (9 mg, 58%). LCMS: m/e 705.49 (M+H)+, 2.60 min (method 10). 1H NMR (400 MHz, Acetic acid d4) δ ppm 7.99 (d, J=8.28 Hz, 2H), 7.25 (d, J=8.28 Hz, 2H), 5.33 (d, J=4.77 Hz, 1H), 4.82 (s, 1H), 4.71 (s, 1H), 3.87 (br. s., 4H), 3.56 (d, J=4.27 Hz, 4H), 3.51-3.40 (m, 2H), 3.39-3.22 (m, 2H), 2.86-2.69 (m, 1H), 2.57-2.34 (m, 2H), 2.27-1.18 (m, 22H), 1.72 (s, 3H), 1.16 (s, 3H), 1.10 (s, 3H), 1.04 (s, 3H), 0.98 (s, 3H), 0.96 (s, 3H).

Workup

  1. customThe reaction mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-f88cd2cd33204ef6bee1529b4c44b50f
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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