Acetic Acid → Maytanacine

HRID 338053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338053
[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]

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 12734DiisopropylcarbodiimideHCID 5358230HCID 5358230, Verbindung

Produkt 1

HCID 6443032Maytanacine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 2734571Scandium(III) triflateKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-8 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-007d35ab15cf4b36b9b986d961eb92fe
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889855B2

Notizen zur Reaktion

Wird geladen…