Acetyl chloride → Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate

HRID 927925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927925
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:15]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:14][CH:13]=[C:12]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([NH:5][C:6]1[C:15]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:14][CH:13]=[C:12]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 6367Acetyl chlorideHCID 90071896Methyl 2-amino-3-[2-(tert-butyldimethylsilanyloxymethyl)furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2×

Produkt 1

HCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Acetyl chloride (0.09 mL) was added to a stirred solution of methyl 2-amino-3-[2-(tert-butyldimethylsilanyloxymethyl)furan-3-yl]-6-(2,2-dimethylpropionylamino)-benzoate (Intermediate 35, 0.47 g) in DCM (5 mL) and pyridine (0.16 mL) and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with DCM and washed with water and brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-50% to give methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (0.442 g) as a colourless foam.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-50%

Quellen und Nachweise

ORD-Eintrag
ord-e6897daee7684f769bb187314220ea53
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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