Potassium Nitrate → p-Nitro-D-phenylalanine

HRID 280041

Reaction equation

HRID 280041 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:13]([O-])([O-:15])=[O:14].[K+]>>[N+:13]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C@H:2]([C:10]([OH:12])=[O:11])[NH2:1])=[CH:5][CH:6]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 24434Potassium NitrateHCID 71567D-Phenylalanine

Product 1

HCID 679497p-Nitro-D-phenylalanine

Procedure

D-Phenylalanine (12.0 g, 73 mmol) and potassium nitrate (11 g, 109 mmol) were loaded into a teflon HF apparatus commonly used for the deprotection of peptides. The mixture was treated with liquid HF at approximately 0° C. for one hour. After removal of the HF by vacuum, the residue was dissolved in water and treated with concentrated ammonia until pH 6. The precipitate was recrystallized from hot water. Yield 9.31 g (61%) of a nearly white solid, mp 236.5°-237° C., [α]D25 =-8.63° (c=1.7, 1N HCl).

Workup

  1. additionThe mixture was treated with liquid HF at approximately 0° C. for one hour
  2. customAfter removal of the HF by vacuum
  3. dissolutionthe residue was dissolved in water
  4. additiontreated with concentrated ammonia until pH 6
  5. customThe precipitate was recrystallized from hot water
  6. customYield 9.31 g (61%) of a nearly white solid, mp 236.5°-237° C., [α]D25 =-8.63° (c=1.7, 1N HCl)

Sources & evidence

ORD record
ord-f9c7fc89644c4d14b7b4ea8b0dc5f28e
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Linked notes

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