DL-Serine → HCID 10014501, compound

HRID 1736712Notes

Reaction equation

HRID 1736712 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12](=O)([O-])[O-].[K+].[K+].C(O)C.[NH2:21][CH:22]([C:25]([OH:27])=[O:26])[CH2:23][OH:24]>O>[CH3:12][O:26][C:25](=[O:27])[CH:22]([CH2:23][OH:24])[NH:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 617DL-SerineHCID 702EthanolHCID 11430Potassium CarbonateHCID 118992,4-Dichloronitrobenzene

Product 1

HCID 10014501HCID 10014501, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 15.66 g of 1-fluoro-2-nitrobenzene (VII), 16.87 g of potassium carbonate, 100 ml of 95% ethanol, and 40 ml of water are added 11.66 g of DL-serine. The reaction is stirred at 90° overnight and then cooled. The solvents are removed trader vacuum and the residue is azeotroped with toluene to remove residual water. The resulting solid is washed with ether and toluene to remove unreacted 1-fluoro-2-nitrobenzene. The solid is then stirred for 18 hr at 20°-25° in 80 ml of DMF with 15.34 g of potassium carbonate and 24 ml of iodomethane. Excess iodomethane and DMF are then removed under vacuum and the residue is partitioned between a mixture of methylene chloride, chloroform and water. The organic layers are dried over sodium sulfate and concentrated. Ethyl ether and hexane are added to the residue and the solid is collected and dried to give the title compound, mp 138°-140°; NMR (CDCl3) 2.15, 3.83, 4.10, 4.41, 6.73-6.81, 7.46, 8.22, 8.60 δ.

Workup

  1. temperaturecooled
  2. customThe solvents are removed trader vacuum
  3. customthe residue is azeotroped with toluene
  4. customto remove residual water
  5. washThe resulting solid is washed with ether and toluene
  6. customto remove unreacted 1-fluoro-2-nitrobenzene
  7. stirringThe solid is then stirred for 18 hr at 20°-25° in 80 ml of DMF with 15.34 g of potassium carbonate and 24 ml of iodomethane
  8. customExcess iodomethane and DMF are then removed under vacuum
  9. customthe residue is partitioned between a mixture of methylene chloride, chloroform and water
  10. dry with materialThe organic layers are dried over sodium sulfate
  11. concentrationconcentrated
  12. additionEthyl ether and hexane are added to the residue
  13. customthe solid is collected
  14. customdried

Sources & evidence

ORD record
ord-8a3c9846404a44868a74b2a0449ac0a5
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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