Acetic Anhydride → Nalpha-Acetyl-p-Nitro-L-Phenylalanine Methyl Ester

HRID 280040Notes

Reaction equation

HRID 280040 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:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[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)[NH:6][C:18](=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 11161427Nalpha-Acetyl-p-Nitro-L-Phenylalanine Methyl EsterYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 2 (4.10 g, 15.7 mmol) was suspended in a mixture of distilled pyridine (40 ml) and acetic anhydride (5 ml). A solution formed after several minutes, and stirring was continued overnight. The solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was then extracted with 0.1N HCl, 1M sodium bicarbonate, and water and dried (MgSO4). Precipitation with hexanes gave 3.57 g (85.1%) of a solid melting at 113°-117° C. Recrystallization from ethyl acetate/hexanes gave 2.75 g, mp 118°-120° C., [α]D25 =+15.1° (c=2.1, ethanol).

Workup

  1. customA solution formed after several minutes
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionThe solution was then extracted with 0.1N HCl, 1M sodium bicarbonate, and water
  5. dry with materialdried (MgSO4)
  6. customPrecipitation with hexanes

Sources & evidence

ORD record
ord-d6229fa8f2ba414e886d2977c2826791
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Reaction notes

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