Triethylamine → 4-Nitro-L-phenylalanine methyl ester

HRID 618351Notes

Reaction equation

HRID 618351 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C>C1COCC1>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH2:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 74082814-Nitro-L-phenylalanine methyl esterYield 119.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To p-nitrophenylalanine methyl ester hydrochloride (5 g, 0.019 mole) (Lancaster) in THF (80 mL) and triethylamine (3.88 g, 0.038 mole) was added isobutylchloroformate (2.62 g, 0.019 mole) (Sigma) dropwise at ice bath temperature. The reaction was stirred at room temperature for 3.5 hours. The resulting precipitate was filtered and washed with THF. The solvent from the filtrate was removed under vacuum. The residue was taken up in ethyl acetate. The ethyl acetate portion was worked up with saturated NaHCO3 (1×), H2O (1×), 1N HCl (2×), H2O (2×), dried over MgSO4 and removed under vacuum to yield 5.08 g of p-nitro-phenylalanine methyl ester, N-isobutylcarbamate as a yellow solid.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with THF
  3. customThe solvent from the filtrate was removed under vacuum
  4. dry with materialdried over MgSO4
  5. customremoved under vacuum

Sources & evidence

ORD record
ord-b68a5c795aaf42f0bfe257a610facb6b
Source dataset
uspto-grants-1999_09
Patent number
US05952381

Reaction notes

Loading…