Carbonochloridic acid, octyl ester → HCID 86737703, 화합물

HRID 444198노트

반응식

HRID 444198 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86737703HCID 86737703, 화합물수율 54.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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),

후처리

  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

출처 및 근거

ORD 기록
ord-af0c9591d64c450cbb1b9d14ad76d9d4
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04263294

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