Carbonochloridic acid, octyl ester → HCID 86737703、化合物

HRID 444198ノート

反応式

HRID 444198 の反応式
[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]

参加物

5

反応物 3

HCID 81956Carbonochloridic acid, octyl esterHCID 5358230HCID 5358230、化合物HCID 178418339Butyllithium

生成物 1

HCID 86737703HCID 86737703、化合物収率 54.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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),

後処理

  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

出典と根拠

ORDレコード
ord-af0c9591d64c450cbb1b9d14ad76d9d4
出典データセット
uspto-grants-1981_04
特許番号
US04263294

反応ノート

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