Sulfuric Acid → HCID 5358230, compound

HRID 1449336Notes

Reaction equation

HRID 1449336 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].OS(O)(=O)=O.[CH3:12][CH:13]1[CH:38]2[O:39][C:37]2([CH3:40])[CH:36]([O:41]C(CC(C)C)=O)[CH2:35][C:33](=[O:34])[N:32]([CH3:48])[C:25]2=[C:26]([Cl:31])[C:27]([O:29][CH3:30])=[CH:28][C:23](=[CH:24]2)[CH2:22][C:21]([CH3:49])=[CH:20][CH:19]=[CH:18][CH:17]([O:50][CH3:51])[C:16]2([OH:56])[NH:52][C:53]([O:55][CH:14]1[CH2:15]2)=[O:54]>O1CCCC1.O>[CH3:12][CH:13]1[CH:38]2[O:39][C:37]2([CH3:40])[CH:36]([OH:41])[CH2:35][C:33](=[O:34])[N:32]([CH3:48])[C:25]2=[C:26]([Cl:31])[C:27]([O:29][CH3:30])=[CH:28][C:23](=[CH:24]2)[CH2:22][C:21]([CH3:49])=[CH:20][CH:19]=[CH:18][CH:17]([O:50][CH3:51])[C:16]2([OH:56])[NH:52][C:53]([O:55][CH:14]1[CH2:15]2)=[O:54]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 5477087HCID 5477087, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 5358230HCID 5358230, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

In 1 ml of tetrahydrofuran was dissolved 15 mg of the Antibiotic C-15003 crystals obtained in Example 31 and the solution was cooled to -5° C. Following the addition of 12 mg of lithium aluminum hydride, the mixture was allowed to stand for 2 hours. Then, after the addition of 0.5 m of 1% H2SO4 in water, the reaction mixture was extracted with 2 ml of ethyl acetate. The ethyl acetate layer was washed with water, dried by the addition of anhydrous sodium sulfate and concentrated under reduced pressure. Preparative TLC was carried out on silica gel with ethyl acetate/methanol=19/1 and the absorbing zone in the neighborhood of Rf 0.25 to 0.3 was scraped off, extracted with ethyl acetate containing a small amount of water, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crystals were recovered by filtration and dried. By the above procedure was obtained 10 mg of maytansinol, m.p. 174° C.

Workup

  1. extractionthe reaction mixture was extracted with 2 ml of ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried by the addition of anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with ethyl acetate containing a small amount of water
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe resultant crystals were recovered by filtration
  10. customdried

Sources & evidence

ORD record
ord-28736ebdc2db414fbbf0bbeb5d3cc0c7
Source dataset
uspto-grants-1980_02
Patent number
US04190580

Reaction notes

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