Water → HCID 136335802, compound

HRID 646464Notes

Reaction equation

HRID 646464 reaction equation
B(Cl)(Cl)Cl.C([O:9][C:10](=[O:49])[CH:11]=[CH:12][C:13]1[CH:18]=[C:17]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[C:20]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:16]([O:33]CC2C=CC=CC=2)=[CH:15][C:14]=1[O:41]CC1C=CC=CC=1)(C)(C)C.C(=O)=O.CC(C)=O.O>ClCCl.C(OCC)(=O)C>[OH:41][C:14]1[CH:15]=[C:16]([OH:33])[C:17]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[C:20]=2[C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[CH:18][C:13]=1[CH:12]=[CH:11][C:10]([OH:49])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 25135Boron TrichlorideHCID 18522661Acetone cardiceHCID 68450766HCID 68450766, compound

Product 1

HCID 136335802HCID 136335802, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Boron trichloride solution (2 ml, 11.0M in dichloromethane) was added slowly to a solution of 3-{2,4-Bis-benzyloxy-5-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-phenyl}acrylic acid tert-butyl ester (50 mg, 0.09 mmol) in dichloromethane (1 ml), at −78° C. (dry ice/acetone) under a nitrogen atmosphere. The resulting solution was stirred for ˜1 hr at −78° C., and for ˜90 mins. at room temperature. The solution was cooled to −78° C. and water (2 ml) added and the mixture was stirred for ˜30 mins at room temperature. Ethyl acetate (30 ml) was added and the solution washed with water (2×5 ml) and saturated aqueous sodium chloride solution (10 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to a pale yellow gum. Trituration with hexane gave a yellow solid, solids were removed by filtration and washed with hexane, dried in vacuo, to give 3-{2,4-dihydroxy-5-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-phenyl}-acrylic acid (10 mg) as yellow powder.

Workup

  1. waitfor ˜90 mins
  2. customat room temperature
  3. temperatureThe solution was cooled to −78° C.
  4. stirringthe mixture was stirred for ˜30 mins at room temperature
  5. washthe solution washed with water (2×5 ml) and saturated aqueous sodium chloride solution (10 ml)
  6. dry with materialThe solution was dried over anhydrous magnesium sulphate
  7. concentrationconcentrated to a pale yellow gum
  8. customTrituration with hexane gave a yellow solid, solids
  9. customwere removed by filtration
  10. washwashed with hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-66a0f51de0da42c68d826309dfa65c79
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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