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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 85715Generated: October 25, 2026

Sodium Hydroxide → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1,1-dioxidotetrahydrothiophen-3-yl)amino)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)benzoic acid

https://huagongshe.com/reaction/85715

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
ReactantHCID 68358224HCID 68358224—
Solvent1,4-DioxaneHCID 31275—
Product4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1,1-dioxidotetrahydrothiophen-3-yl)amino)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)benzoic acidHCID 6835816066%

Reaction Conditions

Temperature78 °C

Reaction Steps

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1,1-dioxidotetrahydrothiophen-3-yl)amino)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)benzoate (40 mg, 0.057 mmol) and sodium hydroxide (0.567 mL, 0.567 mmol) in dioxane (1 mL) was heated up at 78° C. for 3 hours. The reaction mixture was cooled to room temperature, filtered and the clear solution was purified by HPLC to provide the title compound as a white solid (26 mg, 63%). LCMS: m/e 691.46 (M+H)+, 2.24 min (method 11). 1H NMR (500 MHz, Acetic) δ 8.04 (d, J=8.2 Hz, 2H), 7.30 (d, J=8.2 Hz, 2H), 5.37 (d, J=4.9 Hz, 1H), 4.87 (s, 1H), 4.75 (s, 1H), 4.06 (quin, J=7.7 Hz, 1H), 3.67-3.45 (m, 4H), 3.44-3.34 (m, 1H), 3.33-3.11 (m, 2H), 2.92-2.80 (m, 1H), 2.77-2.59 (m, 1H), 2.42-2.29 (m, 1H), 2.26-1.02 (m, 23H), 1.77 (s, 3H), 1.22 (s, 3H), 1.13 (s, 3H), 1.10 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846647B2
Source datasetuspto-grants-2014_09
ORD IDord-09ebaea76ab74c5e881074f98b1e8a00
Source noteuspto-grants-2014_09