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

HRID 1879586Notes

Reaction equation

HRID 1879586 reaction equation
[CH3:1][CH:2]([C@H:4]1[CH:8]2[CH:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:31]([OH:33])=[O:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[CH:12]([C@:13]2([CH3:30])[CH:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)[CH3:3].C(Cl)(Cl)Cl.[CH3:38][OH:39]>>[CH3:3][CH:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:31]([OH:33])=[O:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([O:29][C:38]([CH2:6][C:7]([C:31]([OH:33])=[O:32])([CH3:24])[CH3:8])=[O:39])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)[CH3:1]

Participants

3

Reactant 2

HCID 21584188Chloroform methanolHCID 44337790HCID 44337790, compound

Product 1

HCID 461261(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 acidYield 24.5%

Procedure

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.

Workup

  1. customcrystallization from MeOH-H2O
  2. customgave colorless needles

Sources & evidence

ORD record
ord-ceb11b0cdc2047f9b0aed901622c7e93
Source dataset
uspto-grants-2012_11
Patent number
US08318425B2

Reaction notes

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