Sulfuric Acid → Temsirolimus

HRID 406966

反応式

HRID 406966 の反応式
[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:64][CH3:65])[C:8]([CH3:63])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:62])[CH2:15][C@@H:16]([CH3:61])[C:17]([C@H:19]([O:59][CH3:60])[C@H:20]([OH:58])[C:21]([CH3:57])=[CH:22][C@@H:23]([CH3:56])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([OH:55])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1.[CH3:66][C:67]1([C:79](O)=[O:80])[CH2:72][O:71]C2(CCCCCC2)[O:69][CH2:68]1.S(=O)(=O)(O)O.CCCCCC>C1COCC1.[Cl-].[Na+].O>[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:64][CH3:65])[C:8]([CH3:63])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:62])[CH2:15][C@@H:16]([CH3:61])[C:17]([C@H:19]([O:59][CH3:60])[C@H:20]([OH:58])[C:21]([CH3:57])=[CH:22][C@@H:23]([CH3:56])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([O:55][C:68]([C:67]([CH2:79][OH:80])([CH2:72][OH:71])[CH3:66])=[O:69])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8058HexaneHCID 5284616SirolimusHCID 671751963-Methyl-1,5-dioxaspiro[5.6]dodecane-3-carboxylic acid

生成物 1

HCID 6918289Temsirolimus

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
2.5 °C

実験手順

(160 mg) of 42-ester of rapamycin with 3-methyl-1,5-dioxaspiro[5.6]dodecane-3-carboxylic acid [IId6] was dissolved in 4 ml THF and was cooled it at 0-5° C. Subsequently, 0.5 ml 2N sulphuric acid was added and the reaction mass was stirred at 30-35° C. for 20 hrs. After completion of the reaction brine solution was added and extracted by ethyl acetate. Organic layer was separated and wash it with sodium bicarbonate solution and then by water. Dried by adding sodium sulfate and concentrate it on rotavapour to get colorless viscous oily product. Subsequently, n-hexane was added and stirred for 30 minute. White solid was precipitated, which was filtered, washed with n-hexane to get white solid product.

後処理

  1. additionwas added
  2. extractionextracted by ethyl acetate
  3. customOrganic layer was separated
  4. washwash it with sodium bicarbonate solution
  5. customDried
  6. additionby adding sodium sulfate
  7. concentrationconcentrate it on rotavapour
  8. customto get colorless viscous oily product
  9. stirringstirred for 30 minute
  10. customWhite solid was precipitated
  11. filtrationwhich was filtered
  12. washwashed with n-hexane
  13. customto get white solid product

出典と根拠

ORDレコード
ord-5847e2d40706444086fda123e24fc0ec
出典データセット
uspto-grants-2014_06
特許番号
US08754207B2

関連ノート

読み込み中…