Methyl chloroformate → HCID 67356414, compound

HRID 405699Notes

Reaction equation

HRID 405699 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([CH3:18])[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:27])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)N[Si](C)(C)C.[Li].Cl[C:40]([O:42][CH3:43])=[O:41]>O1CCCC1>[CH3:43][O:42][C:40]([N:14]1[C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:28])=[C:8]([CH3:27])[CH:9]=2)=[CH:17][C:16]([C:19]2[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=2)([CH3:18])[O:15]1)=[O:41]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 57426343Lithium bis(trimethylsilyl)amideHCID 67356019HCID 67356019, compound

Product 1

HCID 67356414HCID 67356414, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-methyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (1.3 g) in dry tetrahydrofuran (15 ml) stirred under argon at −78° C., was added lithium hexamethyldisilazane (“LHMDS”) (1 M in hexane) (3.45 ml). The solution was stirred at −78° C. until deprotonation was completed as monitored by thin layer chromatography. Then, to this solution was added methyl chloroformate (0.465 ml) and the reaction mixture was stirred at −78° C. for 2 hours. The mixture was quenched with saturated ammonium chloride and then extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: heptane/diisopropylether 1:1) to give 3-(4-tert-butoxycarbonyl-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-methyl-5H-isoxazole-2-carboxylic acid methyl ester (472 mg) as a yellow foam.

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 2 hours
  2. customThe mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (eluent: heptane/diisopropylether 1:1)

Sources & evidence

ORD record
ord-e9d0eebc5e0a4fcd958f608d3ed984f7
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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