Cyanogen Bromide → 2-(2-Amino-5-benzoxazolyl) propionic acid

HRID 2082913Notes

Reaction equation

HRID 2082913 reaction equation
[N:1]#[C:2]Br.[NH2:4][C:5]1[CH:6]=[C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH:8]=[CH:9][C:10]=1[OH:11].[OH-].[Na+]>O>[NH2:1][C:2]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:6][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 12202637HCID 12202637, compound

Product 1

HCID 538720312-(2-Amino-5-benzoxazolyl) propionic acidYield 7.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyanogen bromide (1.06 g., 0.1 mole.) was added to a stirred suspension of 2-(3-amino-4-hydroxyphenyl) propionic acid (1.8 g., 0.1 mole.) in water (100 ml.). The suspension was stirred at room temperature for a further 41 hours. The pH of the suspension as adjusted to 4 by the addition of 50% w/v sodium hydroxide solution. The suspension was filtered and the solid was washed (X2) with small volumes of water. Recrystallisation of the solid from 50% aqueous methanol gave 2-(2-amino-5-benzoxazolyl) propionic acid (1.46 g.), m.p. 225° - 229° C.

Workup

  1. additionThe pH of the suspension as adjusted to 4 by the addition of 50%
  2. filtrationThe suspension was filtered
  3. washthe solid was washed (X2) with small volumes of water
  4. customRecrystallisation of the solid from 50% aqueous methanol

Sources & evidence

ORD record
ord-eb46b7bdeda547609b32a49d7a8332cb
Source dataset
uspto-grants-1978_04
Patent number
USRE029608

Reaction notes

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