Betulinic Acid → 9-Acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

HRID 2393068Notes

Reaction equation

[CH3:1][C: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]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].CC([C@H]1[C@@H]2[C@@H]3[C@@](C)(CC[C@@]2(CO)CC1)[C@@]1(C)[C@@H]([C@]2(C)[C@@H](CC1)C(C)(C)[C@@H:49]([OH:62])[CH2:48]C2)CC3)=C>>[CH3:3][C:2]([CH: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]([CH3:27])([CH3:28])[CH:16]([O:29][C:49]([CH3:48])=[O:62])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

Participants

Reactant 2

HCID 64971Betulinic Acid

HCID 72326Betulin

Product 1

HCID 2899849-Acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Procedure

The method of claim 12 wherein the overall yield of the α-isomer of betulinic acid from betulin is greater than 50%.

Sources & evidence

ORD record: ord-61951f038fc84f808da5134a228a2f17
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05804575

Reaction notes

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