Ammonia → HCID 67151589, compound

HRID 1805234Notes

Reaction equation

HRID 1805234 reaction equation
[NH2:1][C@@H:2](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH2:3][OH:4].C([O-])(=O)C.[Na+].[N:21]#[C:22]Br.N>CO>[N+:13]([C:10]1[CH:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[C@H:2]2[CH2:3][O:4][C:22]([NH2:21])=[N:1]2)=[CH:8][CH:9]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 67151550HCID 67151550, compound

Product 1

HCID 67151589HCID 67151589, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (E)-(S)-2-amino-4-(4-nitro-phenyl)-but-3-en-1-ol (2.5 g) in methanol (90 ml) at room temperature was added sodium acetate (3.0 g) followed by a solution of cyanogen bromide (1.65 g) in methanol (10 ml) dropwise over 15 minutes. The reaction mixture was stirred for 2 days, then 25% aqueous ammonia (8.2 ml) was added and the solution stirred for 1 hour at room temperature. The solvent was evaporated in vacuo and the residue purified by Isco chromatography (column: Silicycle Si-Amine, AcOEt) to give (S)-4-[(E)-2-(4-nitro-phenyl)-vinyl]-4,5-dihydro-oxazol-2-ylamine (950 mg) as a yellow oil. MS (ISP): 234.1 ([M+H]+).

Workup

  1. stirringthe solution stirred for 1 hour at room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified by Isco chromatography (column: Silicycle Si-Amine, AcOEt)

Sources & evidence

ORD record
ord-9994e872f83641c7ace36dda7979a1f3
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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