Hydrochloric Acid → HCID 23159857, compound

HRID 2110898Notes

Reaction equation

HRID 2110898 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)[N:3]=1.O[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]C)=[O:32])=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH-].[Na+].Cl>CO.O1CCCC1.O.ClCCl>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][O:21][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:25][CH:24]=3)=[CH:18][CH:19]=2)[N:3]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23159949{4-[(3-methyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol

Product 1

HCID 23159857HCID 23159857, compoundYield 42.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of {4-[(3-methyl-5-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol (139 mg, 0.5 mmol), methyl 3-(4-hydroxyphenyl)propanoate (90 mg, 0.5 mmol), triphenylphosphine (262 mg, 1.0 mmol) and dichloromethane (3 mL) was added dropwise diethyl azodicarboxylate (40% toluene solution, 435 mg, 1.0 mmol) with stirring at room temperature, and the mixture was stirred at room temperature for 1 hr. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2) to give a yellow oil. The yellow oil was dissolved in methanol (3 mL) and tetrahydrofuran (3 mL), and 1 N aqueous sodium hydroxide solution (2 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, and neutralized with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (Manufactured by Wako. Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4) to give the title compound (90 mg, yield 42%, 2 steps) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customAfter completion of the reaction
  3. customthe reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2)
  4. customto give a yellow oil
  5. stirringThe mixture was stirred at room temperature for 1 hr
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4)

Sources & evidence

ORD record
ord-936afb8f3c33442eb25d49b33c826421
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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