Sodium Carbonate → Vinblastine

HRID 553428

反応式

HRID 553428 の反応式
[CH3:1][CH2:2][C@@:3]1([OH:59])[CH2:21][N:19]2[CH2:20][C@H:5]([CH2:6][C@:7]([C:55]([O:57][CH3:58])=[O:56])([C:22]3[CH:23]=[C:24]4[C@:32]56[C@@H:36]7[C@:37]([CH2:52][CH3:53])([C@@H:41]([O:48][C:49]([CH3:51])=[O:50])[C@:42]([OH:47])([C:43]([O:45][CH3:46])=[O:44])[C@@H:31]5[N:30]([CH3:54])[C:25]4=[CH:26][C:27]=3[O:28][CH3:29])[CH:38]=[CH:39][CH2:40][N:35]7[CH2:34][CH2:33]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:9]=3[CH2:17][CH2:18]2)[CH2:4]1.OS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][CH2:2][C@@:3]1([OH:59])[CH2:21][N:19]2[CH2:20][C@H:5]([CH2:6][C@:7]([C:55]([O:57][CH3:58])=[O:56])([C:22]3[CH:23]=[C:24]4[C@:32]56[C@@H:36]7[C@:37]([CH2:52][CH3:53])([C@@H:41]([O:48][C:49]([CH3:51])=[O:50])[C@:42]([OH:47])([C:43]([O:45][CH3:46])=[O:44])[C@@H:31]5[N:30]([CH3:54])[C:25]4=[CH:26][C:27]=3[O:28][CH3:29])[CH:38]=[CH:39][CH2:40][N:35]7[CH2:34][CH2:33]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:9]=3[CH2:17][CH2:18]2)[CH2:4]1

参加物

4

反応物 2

HCID 10340Sodium CarbonateHCID 5388983Vinblastine Sulfate2 回

生成物 1

HCID 13342Vinblastine収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Vinblastine sulfate was purchased from Asian Talent. A 610-mg sample of vinblastine sulfate was dissolved in 20 mL of dichloromethane and then it was shaken with 20 mL of 5% aqueous sodium carbonate. The organic layer was separated and aqueous solution was extracted with dichloromethane (2×20 mL) and then with chloroform (20 mL). The combined organic layer and extracts were dried over sodium sulfate and evaporated to dryness, affording 526 mg (97%) of vinblastine free base as a sticky white solid. The purity of vinblastine free base was checked by 1H 300 MHz NMR and HPLC (99.1% AUC) using a Varian CHROMSEP HPLC column SS 250×4.6 mm including holder with guard column, MICROSORB 100-5 C18; gradient: 30/70 (0.1% trifluoroacetic acid in acetonitrile)/(0.1% trifluoroacetic acid in water) to 100/0 (0.1% trifluoroacetic acid in acetonitrile)/(0.1% trifluoroacetic acid in water); detection at 254 nm and 270 nm.

後処理

  1. customThe organic layer was separated
  2. extractionaqueous solution was extracted with dichloromethane (2×20 mL)
  3. dry with materialThe combined organic layer and extracts were dried over sodium sulfate
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-7efd57db705e42b4904f203238bd83f2
出典データセット
uspto-grants-2011_11
特許番号
US08048872B2

関連ノート

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