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

HRID 888711Notes

Reaction equation

HRID 888711 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].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.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

8

Reactant 6

HCID 1061PhosphateHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 6249AmpicillinHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 656894isopropyl beta-D-thiogalactopyranosideHCID 15239356N-methyl-2-(2-methylphenyl)-2-oxoacetamide

Product 1

HCID 669364422-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamideYield 74.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the plasmid pTrcGSRs, 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 0.5 g of wet bacterial cells. To a reaction tube were added 30 mg of 2-(2-methyl-phenyl)-N-methyl-2-oxo-acetamide, 0.5 g of the wet bacterial cells, 30 mg of NADP+, 45 mg of glucose, and 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 24 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 22.5 mg of oily 2-(2-methyl-phenyl)-N-methyl-2-hydroxy-acetamide. 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 0.5 g of wet bacterial cells
  3. customthese were reacted at a stirring rate of 1000 rpm at 30° C. for 24 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-4cf9e1c6dea8445593902a4f0fc42049
Source dataset
uspto-grants-2012_08
Patent number
US08252563B2

Reaction notes

Loading…