Methanol → Methyl 2-amino-3-(4-nitrophenyl)propanoate

HRID 1869778Notes

Reaction equation

HRID 1869778 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].O=S(Cl)Cl.[CH3:20]O>>[NH2:10][CH:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)[C:11]([O:13][CH3:20])=[O:12]

Participants

4

Reactant 3

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

Product 1

HCID 560520Methyl 2-amino-3-(4-nitrophenyl)propanoate

Procedure

To a suspension of 4-nitrophenylalanine 1 (25 g) in methanol (10 ml/g) at 0° C. is added SOCl2 (2 equ.). After 30 minutes, the reaction is stirred at room temperature for 1 night. Volatiles are then evaporated and the residue is diluted in water. The solution is alkalinized with NaOH 2N and extracted with CH2Cl2. The organic phase is dried over MgSO4 and evaporated. No further purification is needed.

Workup

  1. customVolatiles are then evaporated
  2. additionthe residue is diluted in water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase is dried over MgSO4
  5. customevaporated
  6. customNo further purification

Sources & evidence

ORD record
ord-6073044826314e0293aa2d3dd5eab324
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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