tert-Butanol → HCID 72698479, compound

HRID 1623714Notes

Reaction equation

P(N=[N+]=[N-])(=O)([O:9][C:10]1C=CC=CC=1)OC1C=CC=CC=1.C([N:22](CC)CC)C.[CH3:27][C:28]1[C:32](C(O)=O)=[CH:31][O:30][N:29]=1.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>>[CH3:27][C:28]1[C:32]([NH:22][C:10](=[O:9])[O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:31][O:30][N:29]=1

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 123414Diphenylphosphoryl azide

HCID 45896923-Methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 72698479HCID 72698479, compound

Conditions

Temperature: 90 °C

Procedure

Diphenyl phosphorazidate (1083 mg, 3.93 mmol) and triethylamine (0.55 ml, 3.93 mmol) were added to a stirred solution of 3-methylisoxazole-4-carboxylic acid (500 mg, 3.93 mmol) in tert-butanol (30 ml) at 50° C. After addition, the solution was heated at 90° C. for 6 hours. The reaction mixture was evaporated to remove solvent and the residue was purified by chromatography column (silica gel, 40 g, eluent: dichloromethane/methanol=50:1, 500 ml) to yield the title compound as a white solid. 517 mg.

Workup

additionAfter addition
customThe reaction mixture was evaporated
customto remove solvent
customthe residue was purified by chromatography column (silica gel, 40 g, eluent: dichloromethane/methanol=50:1, 500 ml)

Sources & evidence

ORD record: ord-027d4d9ea61947dcae8e530570c98204
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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