tert-Butanol → Tert-butyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate

HRID 45593Notes

Reaction equation

HRID 45593 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[CH3:41][C:42]([OH:45])([CH3:44])[CH3:43]>>[C:42]([O:45][C:39](=[O:24])[NH:36][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)([CH3:44])([CH3:43])[CH3:41]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 66577242Tert-butyl (5-(4-bromophenyl)-3-methylisoxazol-4-yl)carbamate

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (1.6 g, 6.0 mmol), diphenylphosphoryl azide (1.6 g, 6.0 mmol), and triethylamine (1.3 mL, 9.3 mmol) were combined in t-BuOH and refluxed overnight. After cooling, the mixture was concentrated, and the residue was partitioned between EtOAc and H2O. The organic layer was separated and concentrated, and the residue was purified by silica gel chromatography (16-18% EtOAc in hexanes) to give the title compound.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customthe residue was partitioned between EtOAc and H2O
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (16-18% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b56041ae175a454ea003dbc6def92ec1
Source dataset
uspto-grants-2013_09
Patent number
US08541587B2

Reaction notes

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