Phosphate → 2-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamide

HRID 215703

Reaction equation

HRID 215703 reaction equation
CC(S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C.CC1(C)S[C@@H]2[C@H](NC([C@H](N)C3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O.[CH3:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[C:47](=[O:52])[C:48]([NH:50][CH3:51])=[O:49].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O)C=2N=1.P([O-])([O-])([O-])=O>C(OCC)(=O)C>[CH3:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH:47]([OH:52])[C:48]([NH:50][CH3:51])=[O:49]

Participants

7

Reactant 5

HCID 1061PhosphateHCID 5884NADPHHCID 6249AmpicillinHCID 656894isopropyl beta-D-thiogalactopyranosideHCID 15239356N-methyl-2-(2-methylphenyl)-2-oxoacetamide

Product 1

HCID 669364422-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-549572804a70462485547e6e2184e2a3
Source dataset
uspto-grants-2012_06
Patent number
US08192967B2

Linked notes

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