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

反応式

HRID 990090 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].[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]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 64971Betulinic Acid

生成物 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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3eec6b9af0db43c7a9739402302ea901
出典データセット
uspto-grants-2002_10
特許番号
US06458834B2

関連ノート

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