Sulfuric Acid → Temsirolimus

HRID 406966

Reaktionsgleichung

Reaktionsgleichung von HRID 406966
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 6918289Temsirolimus

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5847e2d40706444086fda123e24fc0ec
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754207B2

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