Reaktion #302885

ord-549572804a70462485547e6e2184e2a3

Reaktionsgleichung

CNC(=O)C(=O)c1ccccc1C
2-(2-methyl-phenyl)-N-methyl-2-oxo-acetamide
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
O=P([O-])([O-])[O-]
phosphate
CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
IPTG
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
ampicillin
CNC(=O)C(O)c1ccccc1C
2-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamide

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstige(37° C., 15 hours)
  2. 2
    Sonstigeto obtain 0.1 g of wet bacterial cells
  3. 3
    Sonstigethese were reacted at a stirring rate of 1000 rpm at 30° C. for 20 hours
  4. 4
    workup.ADDITIONwas added to the reaction solution
  5. 5
    Sonstige(1000×g, 5 minutes)
  6. 6
    Sonstigeto recover an organic layer
  7. 7
    workup.DISTILLATIONThe organic layer was distilled off

Vorschrift

Using the plasmid pTrcGSRxc, E. coli HB101 was transformed. The resulting transformant was inoculated in a sterilized LB medium (100 ml) containing 0.1 mM of IPTG and 50 μg/ml of ampicillin, and was shaking-cultured (37° C., 15 hours). The resulting culture was centrifuged to obtain 0.1 g of wet bacterial cells. To a reaction tube were added 1.5 mg of 2-(2-methyl-phenyl)-N-methyl-2-oxo-acetamide, 0.1 g of the wet bacterial cells, 10 mg of NADPH, and 1.5 ml of a 100 mM phosphate buffer solution (pH 7), and these were reacted at a stirring rate of 1000 rpm at 30° C. for 20 hours. After the completion of the reaction, 5 ml of ethyl acetate was added to the reaction solution, and this was centrifuged (1000×g, 5 minutes) to recover an organic layer. The organic layer was distilled off to obtain oily 2-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamide. Content analysis by liquid chromatography under the following condition showed that the conversion rate was 87.2%. 1H-NMR analysis result of the resulting 2-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamide is shown below.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08192967B2uspto-grants-2012_06