Triethylamine → Ethyl 5-(3-((tert-butoxycarbonyl)amino)phenyl)isoxazole-3-carboxylate

HRID 1375659Notes

Reaction equation

HRID 1375659 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[CH:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][CH2:18][O:19][C:20](/[C:22](/Cl)=[N:23]\[OH:24])=[O:21].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.Cl>[CH2:18]([O:19][C:20]([C:22]1[CH:15]=[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16])[CH:9]=2)[O:24][N:23]=1)=[O:21])[CH3:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 11275982tert-Butyl 3-ethynylphenylcarbamate

Product 1

HCID 49775748Ethyl 5-(3-((tert-butoxycarbonyl)amino)phenyl)isoxazole-3-carboxylateYield 69.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-ethynyl-phenyl)-carbamic acid tert-butyl ester (2.48 g, 0.0114 mole) and ethyl chlorooximidoacetate (3.82 g, 0.0252 mole) were mixed in THF (12 mL) and triethylamine (3.98 mL, 0.0286 mole) was added slowly. The mixture was stirred for 16 hours and then diluted with ethyl acetate (100 mL) and aqueous 1N HCl (50 mL). The two layers were separated and the aqueous layer extracted with ethyl acetate (2×50 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated in vacuo and purified by flash chromatography (10–15% ethyl acetate/Hexane) to provide the titled compound (2.64 g, 50% yield).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer extracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organics were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (10–15% ethyl acetate/Hexane)

Sources & evidence

ORD record
ord-f7cc28789b104eed8ee397c60fb8c163
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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