2-Dimethylaminopyridine → (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(4-hydroxy-2,2-dimethyl-4-oxo-butanoyl)oxy-1-isopropenyl-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 1489905

反応式

HRID 1489905 の反応式
[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].[CH3:34]N(C1C=CC=CN=1)C.C[CH:44]1[C:49](=[O:50])[O:48][C:46](=[O:47])[CH:45]1[CH3:51].C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[CH3:3][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]([CH3:27])([CH3:28])[C@@H:16]([O:29][C:46]([C:45]([CH2:44][C:49]([OH:48])=[O:50])([CH3:51])[CH3:34])=[O:47])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

参加物

6

反応物 4

HCID 218852-DimethylaminopyridineHCID 64971Betulinic AcidHCID 1401452,3-Dimethylsuccinic anhydrideHCID 21584188Chloroform methanol

生成物 1

HCID 461257(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(4-hydroxy-2,2-dimethyl-4-oxo-butanoyl)oxy-1-isopropenyl-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収率 3.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-O-(2',2'-dimethylsuccinyl)betulinic acid (2) was prepared as above using a solution of betulinic acid, dimethylaminopyridine, and dimethylsuccinic anhydride in anhydrous pyridine. The yield was 3.1%. Crystallization form methanol gave colorless needles, melting point 279°-280° C.; [α]D19 +36.2° [c=0.35, CHCl3-MeOH (1:1)]; positive FABMS m/z 585 (M+H)+ ; Negative FABMS m/z 583 (M-H)- ; HR-FABMS calculated for C36H57O6 585.4155, found m/z 585.4156; 1H NMR (pyridine-d5): 0.75, 0.93, 1.03 (×2), 1.06 (each 3H, s; 4-(CH3)2, 8-CH3, 10-CH3, 14-CH3), 1.49 (6H, 2, 2'-CH3 ×2), 1.80 (3H, s, 20-CH3), 2.94 (2H, s, H2-3'), 3.55 (1H, m, H-19), 4.77 (1H, dd, J=5, 11.5 Hz, H-3), 4.79, 4.95 (each 1H, br s, H-30).

後処理

  1. customCrystallization
  2. customform methanol
  3. customgave colorless needles, melting point 279°-280° C.

出典と根拠

ORDレコード
ord-cc6a98c211b34de2b0caef8d2a276bf8
出典データセット
uspto-grants-1997_10
特許番号
US05679828

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