Diethyl Pyrocarbonate → 3-(4-Tert-butylphenyl)propynoic acid 3-fluoro-4-methanesulfonylamino-5-vinylbenzylamide

HRID 2358393Notes

Reaction equation

HRID 2358393 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]([OH:15])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:16][CH2:17][C:18]1[CH:23]=[C:22]([CH:24]=[CH2:25])[C:21]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[C:20]([F:31])[CH:19]=1.CCOC(OC(OCC)=O)=O.CCCCCC.CCOC(C)=O>CN(C=O)C>[F:31][C:20]1[CH:19]=[C:18]([CH:23]=[C:22]([CH:24]=[CH2:25])[C:21]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:17][NH:16][C:13](=[O:15])[C:12]#[C:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 113447013-(4-tert-butylphenyl)prop-2-ynoic AcidHCID 21226206Ethyl acetate hexaneHCID 57665528HCID 57665528, compound

Product 1

HCID 118525773-(4-Tert-butylphenyl)propynoic acid 3-fluoro-4-methanesulfonylamino-5-vinylbenzylamideYield 72.25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-tert-Butylphenyl)propynoic acid (step 2 of Example 11, 0.16 mmol, 33.0 mg) and N-(4-aminomethyl-2-fluoro-6-vinylphenyl)methanesulfonamide (step 6 of Example 2, 0.19 mmol, 39.20 mg), DEPC (1.2 eq, 0.19 mmol, 29.13 μl), TEA (2 eq, 0.32 mmol, 44.60 μl) in DMF under an Ar atmosphere was stirred at room temperature for 12 h. Upon completion, as determined by TLC, the reaction solution was extracted by EtOAc (150 ml×3) and the organic phase was washed with H2O, dried (Na2SO4), filtered and concentrated. After silica gel column chromatography (n-hexane/EtOAc=2:1), 3-(4-tert-butylphenyl)propynoic acid 3-fluoro-4-methanesulfonylamino-5-vinylbenzylamide (49.5 mg, 0.11 mmol, 72.25%) was isolated.

Workup

  1. extractionthe reaction solution was extracted by EtOAc (150 ml×3)
  2. washthe organic phase was washed with H2O
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-46f2487ff0b1475e932a749834102d01
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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