Triphenylphosphine → methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylate

HRID 1026206Notes

Reaction equation

HRID 1026206 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.O[CH2:12][C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:18]([O:17][C:16]([NH:15][C@@H:13]([CH3:14])[CH2:12][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1)=[O:22])([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 178498603HCID 178498603, compound

Product 1

HCID 67778409methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylateYield 59.6%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-hydroxyisoxazole-5-carboxylate (20 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (25 g) and triphenylphosphine (55.1 g) in THF (800 mL) was added dropwise a toluene solution (1.9 M, 110 mL) of diisopropyl azodicarboxylate, and the mixture was refluxed for 5 hr. The reaction mixture was allowed to cool to room temperature, and ethyl acetate was added thereto. The mixture was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (25 g).

Workup

  1. temperaturethe mixture was refluxed for 5 hr
  2. washThe mixture was washed with water and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2d10437e09f74f57982ff9e90e6283ae
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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