Acetic Acid → Maytanacine

HRID 338053노트

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HRID 338053 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: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]

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 12734DiisopropylcarbodiimideHCID 5358230HCID 5358230, 화합물

생성물 1

HCID 6443032Maytanacine

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 2734571Scandium(III) triflate촉매HCID 6344Dichloromethane용매

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온도
-8 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-007d35ab15cf4b36b9b986d961eb92fe
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889855B2

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