Water → HCID 86739165, compound

HRID 2295277Notes

Reaction equation

HRID 2295277 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].[CH:40]1([C:44]([OH:46])=[O:45])[CH2:43][CH2:42][CH2:41]1.O>ClCCl.CN(C)C1C=CN=CC=1>[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].[CH2:42]1[CH2:43][CH:40]([C:44]([O-:46])=[O:45])[CH2:41]1

Participants

6

Reactant 3

HCID 962WaterHCID 19494Cyclobutanecarboxylic acidHCID 5358230HCID 5358230, compound

Product 1

HCID 86739165HCID 86739165, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Maytansinol (127.7 mg) and cyclobutanecarboxylic acid (120 μl) was dissolved in 5 ml of dichloromethane. To the solution, were added 340 mg of N,N-dicyclohexylcarbodiimide and 55 mg of 4-dimethylaminopyridine. The mixture was stirred at room temperature for four hours. To the reaction solution was added water, and the mixture was stirred. The resulting precipitates were removed by filtration and the filtrate was diluted with ethyl acetate. The ethyl acetate layer was separated and washed with water and dried. The solvent was removed by evaporation and the residue was purified by means of a silica-gel chromatography (solvent: aqueous ethyl acetate) to collect 82.7 g of a fraction containing the desired product. The product was crystallized from a small volume of ethyl acetate to yield 47.6 mg of maytansinol 3-cyclobutanecarboxylate. Melting point: 205°-208° C. (decomp.).

Workup

  1. stirringthe mixture was stirred
  2. customThe resulting precipitates
  3. customwere removed by filtration
  4. additionthe filtrate was diluted with ethyl acetate
  5. customThe ethyl acetate layer was separated
  6. washwashed with water
  7. customdried
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by means of a silica-gel chromatography (solvent: aqueous ethyl acetate)
  10. customto collect 82.7 g of a fraction
  11. additioncontaining the desired product
  12. customThe product was crystallized from a small volume of ethyl acetate

Sources & evidence

ORD record
ord-39c308424b3f40c19c0ac8610fa372f7
Source dataset
uspto-grants-1984_01
Patent number
US04424219

Reaction notes

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