Sodium Hydroxide → HCID 78320690, compound

HRID 1773038Notes

Reaction equation

HRID 1773038 reaction equation
[O:1]=[S:2]1(=[O:52])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH:10][C@:11]23[CH2:48][CH2:47][C@@H:46]([C:49]([CH3:51])=[CH2:50])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:45])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C:20](/[CH:33]=[CH:34]/[C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41]C)=[O:40])=[CH:37][CH:36]=3)=[CH:19][CH2:18]4)[CH2:15][CH2:14]2)[CH2:4][CH2:3]1.[OH-].[Na+]>O1CCOCC1.CO>[O:52]=[S:2]1(=[O:1])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH:10][C@:11]23[CH2:48][CH2:47][C@@H:46]([C:49]([CH3:51])=[CH2:50])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:45])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:31])([CH3:32])[C:20](/[CH:33]=[CH:34]/[C:35]3[CH:36]=[CH:37][C:38]([C:39]([OH:41])=[O:40])=[CH:43][CH:44]=3)=[CH:19][CH2:18]4)[CH2:15][CH2:14]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86731497HCID 86731497, compound

Product 1

HCID 78320690HCID 78320690, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-((E)-2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)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)vinyl)benzoate (35 mg, 0.048 mmol) in dioxane (2 mL) and MeOH (1 mL) was added 1N NaOH (1 mL, 1 mmol). The mixture was stirred at 50° C. for 2 h. The crude product was purified by prep HPLC (method 4) to give 4-((E)-2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)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)vinyl)benzoic acid as a white solid (12 mg, 35.0%). MS: m/e 717.5 (M+H)+, 2.798 min (method 4). 1H NMR (400 MHz, CHLOROFORM-d) δ 8.08-7.95 (m, 2H), 7.47 (br. s., 2H), 6.98-6.83 (m, 1H), 6.77-6.64 (m, 1H), 5.87 (d, J=4.8 Hz, 1H), 4.72 (br. s., 1H), 4.61 (br. s., 1H), 3.27-3.06 (m, 8H), 2.95 (d, J=7.3 Hz, 2H), 2.86-2.62 (m, 3H), 2.23-2.00 (m, 3H), 1.98-1.79 (m, 4H), 1.73 (br. s., 3H), 1.66-1.50 (m, 5H), 1.48-1.18 (m, 10H), 1.11 (s, 3H), 1.09-1.05 (m, 3H), 1.03-0.96 (m, 6H), 0.76 (s, 3H).

Workup

  1. customThe crude product was purified by prep HPLC (method 4)

Sources & evidence

ORD record
ord-6157e28fc19e467fa929e6ac65bb80c8
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

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