Triethylamine → N-((Methoxycarbonyl)methyl)4-Nitrophenylalanine Methyl Ester

HRID 719663Notes

Reaction equation

HRID 719663 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:24])[C@H:12]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[NH2:13].[CH3:25][O:26][C:27](=[O:30])[CH2:28]Br>C1COCC1>[CH3:9][O:10][C:11](=[O:24])[C@H:12]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[NH:13][CH2:28][C:27]([O:26][CH3:25])=[O:30]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 60984Methyl bromoacetateHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 68574020N-((Methoxycarbonyl)methyl)4-Nitrophenylalanine Methyl EsterYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (22 mmol) was added to a suspension of 4-Nitrophenylalanine methyl ester hydrochloride (2) (21 mmol) in THF (50 ml). The mixture was stirred at room temperature for one hour, the triethylamine hydrochloride was filtered off, and the filtrate concentrated to yellow oil. The oil was dissolved in dry THF (50 ml) and to this solution was added triethylamine (60 mmol) and methylbromoacetate (60 mmol), the solution was stirred at room temperature under nitrogen atmosphere for 3 hours, after which the precipitate was filtered off and the filtrate concentrated on vacuum. The residue was dissolved in ethylacetate, washed with H2O, dried (MgSO4) and concentrated on vacuum to give yellow oil. The yield was 92%.

Workup

  1. filtrationthe triethylamine hydrochloride was filtered off
  2. concentrationthe filtrate concentrated to yellow oil
  3. dissolutionThe oil was dissolved in dry THF (50 ml) and to this solution
  4. stirringthe solution was stirred at room temperature under nitrogen atmosphere for 3 hours
  5. filtrationafter which the precipitate was filtered off
  6. concentrationthe filtrate concentrated on vacuum
  7. dissolutionThe residue was dissolved in ethylacetate
  8. washwashed with H2O
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated on vacuum
  11. customto give yellow oil

Sources & evidence

ORD record
ord-1d361a77553743f0b595134964d1542c
Source dataset
uspto-grants-2006_11
Patent number
US07132513B2

Reaction notes

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