Methanol → 4-Nitro-L-phenylalanine methyl ester

HRID 1805407Notes

Reaction equation

HRID 1805407 reaction equation
O=S(Cl)Cl.[N+:5]([C:8]1[CH:19]=[CH:18][C:11]([CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH3:20]O>>[CH3:20][O:16][C:15](=[O:17])[C@H:13]([CH2:12][C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:19][CH:18]=1)[NH2:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 137064-Nitro-3-phenyl-L-alanineHCID 24386Thionyl Chloride

Product 1

HCID 74082814-Nitro-L-phenylalanine methyl esterYield 97%

Procedure

10 mL of SOCl2 and 40 mL of methanol were thoroughly mixed in an ice bath for 30 minutes, followed by mixing with 0.51 g of p-nitrophenylalanine to obtain a reaction solution. The reaction solution was subjected to reflux reaction at 70° C. for 24 hours, followed by evaporating, re-crystallizing in ether, and filtering to obtain a product of 0.53 g (97.0%) of a white solid of NBPDA.

Workup

  1. customto obtain a reaction solution
  2. temperatureto reflux
  3. customreaction at 70° C. for 24 hours
  4. customby evaporating
  5. customre-crystallizing in ether
  6. filtrationfiltering

Sources & evidence

ORD record
ord-5b955cb57e684a928efb94851e839a5e
Source dataset
uspto-grants-2013_01
Patent number
US08354512B2

Reaction notes

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