Carbonochloridic acid, octyl ester → HCID 86737703, compound

HRID 444198Notes

Reaction equation

HRID 444198 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([Li])CCC.ClC(OCCCCCCCC)=[O:47]>C1COCC1>[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].[CH3:5][CH2:4][CH:3]([O:38][C:36](=[O:37])[O-:47])[CH2:2][CH2:27][CH2:26][CH2:25][CH3:24]

Participants

5

Reactant 3

HCID 81956Carbonochloridic acid, octyl esterHCID 5358230HCID 5358230, compoundHCID 178418339Butyllithium

Product 1

HCID 86737703HCID 86737703, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 6.0 ml of dry THF is dissolved 163 mg of maytansinol and under nitrogen gas streams and at -20° C., the solution is treated with 10 molar equivalents of 15% n-butyllithium (n-hexane solution). Then, 556 mg of n-octyl chloroformate is added and the mixture is stirred for 15 minutes. Thereafter, at 0° C., the organic layer is extracted with 1.0 ml of saturated sodium chloride and 20 ml of THF. The organic layer is dried, after which the solvent is distilled off. The residue is purified by silica gel chromatography to obtain 58 mg of maytansinol 3-n-octylcarbonate. Thin layer chromatography on silica gel (Merck HPTLC): Rf=0.61 (developing solvent: chloroform-methanol=95:5),

Workup

  1. extractionThereafter, at 0° C., the organic layer is extracted with 1.0 ml of saturated sodium chloride and 20 ml of THF
  2. customThe organic layer is dried
  3. distillationafter which the solvent is distilled off
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-af0c9591d64c450cbb1b9d14ad76d9d4
Source dataset
uspto-grants-1981_04
Patent number
US04263294

Reaction notes

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