Isobutyric Acid → HCID 11411101、化合物

HRID 338054ノート

反応式

HRID 338054 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:40](O)(=[O:44])[CH:41]([CH3:43])[CH3:42].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[CH3:1][C@H:2]1[C@H:27]2[O:28][C@@:26]2([CH3:29])[C@@H:25]([O:30][C:40]([CH:41]([CH3:43])[CH3:42])=[O:44])[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]

参加物

7

反応物 3

HCID 6590Isobutyric AcidHCID 12734DiisopropylcarbodiimideHCID 5358230HCID 5358230、化合物

生成物 1

HCID 11411101HCID 11411101、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 2734571Scandium(III) triflate触媒HCID 6344Dichloromethane溶媒

反応条件

温度
-8 °C

実験手順

A mixture of maytansinol (6.00 mg, 0.01062 mmol), isobutyric acid (23.60 mg, 0.2124 mmol), Sc(OTf)3 (3.14 mg, 0.00637 mmol) and DMAP (3.89 mg, 0.03186 mmol) in CH2Cl2 (1 mL) was stirred for 0.5 h at −8° C. DIC (29.49 mg, 0.2337 mmol) was added dropwise. The mixture was stirred till completion, quenched with diluted HCl, and extracted with CH2Cl2. The organic layer was washed with aq. NaHCO3, brine, and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. Chromatography (silica gel, CH2Cl2/MeOH 30:1) gave the desired product ansamitocin P3. LC-MS (M+Na+) calc.: 657.3. found: 657.4.

後処理

  1. stirringThe mixture was stirred till completion
  2. customquenched with diluted HCl
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with aq. NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-e29fdcd3fcb947bb9d23f3a6cd9fdff0
出典データセット
uspto-grants-2014_11
特許番号
US08889855B2

反応ノート

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