Water → 3-Azidotyrosine

HRID 1280102Notes

Reaction equation

HRID 1280102 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[OH:14])[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].O.N([O-])=O.[Na+].[N-:20]=[N+:21]=[N-].[Na+]>Cl>[NH2:7][C@@H:6]([CH2:5][C:4]1[CH:11]=[CH:12][C:13]([OH:14])=[C:2]([N:1]=[N+:20]=[N-:21])[CH:3]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 1604503-AminotyrosineHCID 23668193Sodium Nitrite

Product 1

HCID 30355793-Azidotyrosine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-amino-L-tyrosine.2HCl.H2O (2.50 g, 8.8 mmol) in 0.5 N HCl (28 mL) at 0° C., an aqueous solution of NaNO2 (0.724 g, 10.5 mmol, in 10 mL H2O) was added slowly. The reaction mixture was stirred for 10 min at 0° C., in the dark, and then a solution of NaN3 (1.43 g, 21.9 mmol, in 10 mL H2O) was added and stirring was continued for 1 h at 0° C. The white solid formed was filtered and dried to give (S)-2-amino-3-(3-azido-4-hydroxy-phenyl)-propionic acid (1.16 g) as of a beige solid. This amino acid was coupled to the carboxylic acid of example 2 in the usual manner to give the title compound of example 146 after purification by preparative C18 reversed-phase HPLC.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h at 0° C
  3. customThe white solid formed
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-2620cdceae684347a9e50cbf7d97950a
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

Loading…