4-Nitro-3-phenyl-L-alanine → HCID 9996417, compound

HRID 483378Notes

Reaction equation

HRID 483378 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:25]=[CH:24][C:17]([CH2:18][C@@H:19]([C:21](O)=[O:22])[NH2:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].[OH-].[K+]>O>[CH2:1]([N:8]1[C:21](=[O:22])[CH:19]([CH2:18][C:17]2[CH:24]=[CH:25][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)[NH:20][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 137064-Nitro-3-phenyl-L-alanineHCID 14797Potassium HydroxideHCID 76639Benzyl isocyanate

Product 1

HCID 9996417HCID 9996417, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl isocyanate (3.2 g, Aldrich) was added dropwise at 0° C. over 20 minutes to a stirred mixture of p-nitrophenylalanine (4.2 g, Fluka) and KOH (1.3 g) in water (40 ml). When addition was complete, the mixture was stirred at 60°-70° C. for 2 hours, then cooled, filtered, and the filtrate treated with c.HCl. The resulting white solid was filtered off, washed with ice-water, dried in vacuo, then suspended in 50% aqu. HCl (20 ml) and refluxed for 2 hours. The suspension was cooled, diluted with water, filtered, and the residue dried in vacuo to give the desired product (5.7 g).

Workup

  1. additionWhen addition
  2. temperaturecooled
  3. filtrationfiltered
  4. additionthe filtrate treated with c
  5. filtrationThe resulting white solid was filtered off
  6. washwashed with ice-water
  7. customdried in vacuo
  8. temperatureHCl (20 ml) and refluxed for 2 hours
  9. temperatureThe suspension was cooled
  10. additiondiluted with water
  11. filtrationfiltered
  12. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-11a188590fe041c58ec8750c891ac664
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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