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 380316

반응식

HRID 380316 반응식
[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]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 64971Betulinic Acid

생성물 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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eeb66d5179154084b2a55c7b7766ae1e
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303589B1

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