Acetic Anhydride → 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 990090

Reaktionsgleichung

Reaktionsgleichung von HRID 990090
[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].[O:34](C(C)=O)[C:35]([CH3:37])=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[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:35]([CH3:37])=[O:34])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 64971Betulinic Acid

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Betulinic acid, 100 mg (0.22 mmoles) was added to a solution containing 4 mg of 4-dimethylaminopyridine (DMAP) and 0.5 ml of (CH3CO)2O in 5 ml of CH2Cl2. After 2 hrs CH2Cl2 was removed in vacuo, and the remaining residue stirred with 25 ml of water. During the stirring enough of K2CO3 was added to decompose an excess of acetic anhydride, after which the reaction mixture was extracted with 25 ml of CH2Cl2. The extract was evaporated to dryness and the resulting solid crystallized from MeOH to give 104 mg of acetylbetulinic acid as white crystals, m.p. 285° C.

Aufarbeitung

  1. customAfter 2 hrs CH2Cl2 was removed in vacuo
  2. additionDuring the stirring enough of K2CO3 was added
  3. extractionafter which the reaction mixture was extracted with 25 ml of CH2Cl2
  4. customThe extract was evaporated to dryness
  5. customthe resulting solid crystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-3eec6b9af0db43c7a9739402302ea901
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458834B2

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