Acetic Acid → Maytanacine

HRID 338053ノート

反応式

HRID 338053 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:42])[CH3:41].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]([CH3:41])=[O:42])[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 176Acetic AcidHCID 12734DiisopropylcarbodiimideHCID 5358230HCID 5358230、化合物

生成物 1

HCID 6443032Maytanacine

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), acetic acid (12.75 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, 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 P1. LC-MS (M+Na+) calc.: 629.2. found: 629.3.

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-007d35ab15cf4b36b9b986d961eb92fe
出典データセット
uspto-grants-2014_11
特許番号
US08889855B2

反応ノート

読み込み中…