Nitric Acid → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-nitrophenyl)-L-phenylalanine methyl ester

HRID 1060463Notes

Reaction equation

HRID 1060463 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].[N+:34]([O-])([OH:36])=[O:35]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([O:31][CH3:32])=[CH:25][CH:26]=[C:27]([N+:34]([O-:36])=[O:35])[C:28]=2[O:29][CH3:30])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 54326841N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

Product 1

HCID 53824822N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-nitrophenyl)-L-phenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (1.59 g) was dissolved in THF (4 mL) under N2 then 70% HNO3 (4 mL) was added and the mixture was stirred at 50° C. overnight. The mixture was diluted with AcOEt (150 mL) and washed with water (100 mL). The organic layer was dried (MgSO4), filtered and evaporated. The residue was dissolved in anhydrous MeOH (100 mL) and dry HCl gas was bubbled through the mixture at 0° C. for a few minutes. The mixture was stirred at room temperature overnight, concentrated, taken up with AcOEt and washed with 1N HCl, satd. NaHCO3 and brine. The organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified by flash column chromatography (silica gel; eluent: hexanes and AcOEt) to give N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-nitrophenyl)-L-phenylalanine methyl ester (1.1 g).

Workup

  1. washwashed with water (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was dissolved in anhydrous MeOH (100 mL)
  6. customdry HCl gas was bubbled through the mixture at 0° C. for a few minutes
  7. stirringThe mixture was stirred at room temperature overnight
  8. concentrationconcentrated
  9. washwashed with 1N HCl
  10. dry with materialThe organic layer was dried (MgSO4)
  11. filtrationfiltered
  12. customevaporated
  13. customThe crude product was purified by flash column chromatography (silica gel; eluent: hexanes and AcOEt)

Sources & evidence

ORD record
ord-de5e30d8e6b24e8b8d221842269a3eaf
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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