Chloroform methanol → (1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(4-hydroxy-3,3-dimethyl-4-oxo-butanoyl)oxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Chloroform methanol	HCID 21584188	—
Reactant	HCID 44337790	HCID 44337790	—
Product	(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(4-hydroxy-3,3-dimethyl-4-oxo-butanoyl)oxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid	HCID 461261	24.5%

Reaction Steps

yield 24.5% (starting with 155.9 mg of dihydrobetulinic acid); crystallization from MeOH—H2O gave colorless needles; mp 291°-292° C.; [α]D20-13.4° (c=1.1, CHCl3—MeOH [1:1], 1H NMR (pyridine-d5): 0.85, 0.94 (each 3H, d, J=7.0 Hz; 20-(CH3)2), 0.75, 0.93, 0.97, 1.01, 1.03 (each 3H, s; 4-(CH3)2, 8-CH3, 10-CH3, 14-CH3), 1.55 (6H, s; 3′-CH3×2), 2.89, 2.97 (each 1H, d, J=15.5 Hz; H-2′), 4.77 (1H, dd, J=5.0, 11.0 Hz, H-3); Anal. Calcd for C36H58O6.5/2H2O: C 68.43, H 10.04; found C 68.64, H 9.78.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07537765B2
Source dataset	uspto-grants-2009_05
ORD ID	ord-a907d4e900554b118199d363c3f12e7f
Source note	uspto-grants-2009_05