Beta-Alanine → N-(4-Azido-2-nitrophenyl)-beta-alanine

HRID 1738746Notes

Reaction equation

HRID 1738746 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[N+:2]=[N-:3].[NH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].C([O-])([O-])=O.[Na+].[Na+].C(O)C>O>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 702EthanolHCID 10340Sodium CarbonateHCID 931211-Fluoro-2-nitro-4-azidobenzene

Product 1

HCID 15088120N-(4-Azido-2-nitrophenyl)-beta-alanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

4-azido-1-fluoro-2-nitro-benzene (90 mg) is mixed with an aqueous solution (0.5 ml) containing 3-aminopropionic acid (53 mg) and Na2CO3 (106 mg). Following addition of 2 ml of ethanol and 0.5 ml of water, the solution is heated for 24 h at 55° C. After removal of the unreacted materials by several ether extractions, the product (3-(N-(4-azido-2-nitrophenyl)-amino)propionic acid) is obtained by ether extraction of the acidified (pH 2.0) aqueous phase.

Workup

  1. customAfter removal of the unreacted materials
  2. extractionby several ether extractions

Sources & evidence

ORD record
ord-5de9e0014155412f9c39b11774f5d98d
Source dataset
uspto-grants-1999_10
Patent number
US05965106

Reaction notes

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