Isobutyric Acid → HCID 11411101, Verbindung

HRID 338054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338054
[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]

Komponenten

7

Edukt 3

HCID 6590Isobutyric AcidHCID 12734DiisopropylcarbodiimideHCID 5358230HCID 5358230, Verbindung

Produkt 1

HCID 11411101HCID 11411101, Verbindung

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), 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.

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-e29fdcd3fcb947bb9d23f3a6cd9fdff0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889855B2

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