Water → 57103-69-2

HRID 1660105Notes

Reaction equation

HRID 1660105 reaction equation
[CH3:1][CH:2]1[CH:27]2[O:28][C:26]2([CH3:29])[CH:25]([OH:30])[CH2:24][C:22](=[O:23])[N:21]([CH3:31])[C:14]2=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:12](=[CH:13]2)[CH2:11][C:10]([CH3:32])=[CH:9][CH:8]=[CH:7][CH:6]([O:33][CH3:34])[C:5]2([OH:39])[NH:35][C:36]([O:38][CH:3]1[CH2:4]2)=[O:37].[C:40](OC(=O)C)(=[O:42])[CH3:41].O>N1C=CC=CC=1.C(Cl)(Cl)Cl.CO>[CH3:1][C@H:2]1[C@@H:27]2[O:28][C@@:26]2([CH3:29])[C@@H:25]([O:30][C:40]([CH3:41])=[O:42])[CH2:24][C:22](=[O:23])[N:21]([CH3:31])[C:14]2=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:12](=[CH:13]2)[CH2:11][C:10]([CH3:32])=[CH:9][CH:8]=[CH:7][C@@H:6]([O:33][CH3:34])[C@:5]2([OH:39])[NH:35][C:36]([O:38][C@H:3]1[CH2:4]2)=[O:37]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 5358230HCID 5358230, compound

Product 1

HCID 644303257103-69-2

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21584188Chloroform methanolSolvent

Procedure

In 0.7 ml of pyridine was dissolved 100 mg of maytansinol. To the solution, cooled with ice, was added 0.35 ml of acetic anhydride. The mixture was left standing for 18 hours at room temperature (23°-25° C.). The reaction solution was poured into 5 ml of cold water and stirred. The precipitate separated out was collected by filtration and dried to obtain 85 mg of powdery substance. This powdery substance was dissolved in 1 ml of chloroform/methanol 10:1 (V/V). To the solution was added 0.2 g of silica gel, and mixed sufficiently. The mixture was then applied to the top of a silica gel column (80 ml). Elution was carried out with ethyl acetate saturated with water. The eluate was collected in 10 ml fractions. The fractions of No. 37-44 were collected, concentrated under reduced pressure. To the residue was added a small volume of ethyl acetate (about 0.5 ml) to dissolve the precipitating crystals again, then was left standing at room temperature. Precipitating crystals were collected by filtration, whereupon 36.0 mg. of maytanacine was obtained. The melting point of this was 231° C. and, when compared with maytanacine obtained in Reference Example 22 in mass spectrum, IR spectrum, UV-spectrum and thin layer chromatogram, this product was found to be identical with the maytanacine obtained in the above.

Workup

  1. temperatureTo the solution, cooled with ice
  2. waitThe mixture was left
  3. custom(23°-25° C.)
  4. customThe precipitate separated out
  5. filtrationwas collected by filtration
  6. customdried
  7. customto obtain 85 mg of powdery substance
  8. additionTo the solution was added 0.2 g of silica gel
  9. additionmixed sufficiently
  10. washElution
  11. customThe eluate was collected in 10 ml fractions
  12. custom37-44 were collected
  13. concentrationconcentrated under reduced pressure
  14. additionTo the residue was added a small volume of ethyl acetate (about 0.5 ml)
  15. dissolutionto dissolve the precipitating crystals again
  16. waitwas left
  17. customstanding at room temperature
  18. customPrecipitating crystals
  19. filtrationwere collected by filtration, whereupon 36.0 mg

Sources & evidence

ORD record
ord-26c6db082b374bbb9018feba7d2d8cec
Source dataset
uspto-grants-1981_12
Patent number
US04307016

Reaction notes

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