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

HRID 660339Notes

Reaction equation

HRID 660339 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Br[C:15]#[N:16].[OH-].[Na+]>O>[NH2:16][C:15]1[O:8][C:7]2[CH:6]=[CH:5][C:4]([CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

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

Product 1

HCID 538720312-(2-Amino-5-benzoxazolyl) propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2) (630 mg, 1 mmol) in H2O (33 ml) was added BrCN (383 mg, 1.04 mmol) at room temperature. The reaction mixture is stirred for 40 h at room temperature. The reaction mixture is neutralized to pH 6□7 with 40% aq. NaOH and filtered. The solid was recrystallized with 50% aq. MeOH and filtered. The solid is dried under vacuum.

Workup

  1. filtrationfiltered
  2. customThe solid was recrystallized with 50% aq. MeOH
  3. filtrationfiltered
  4. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-b5974317e8f0408399c9859a5e992f7c
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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