Acetic Acid → HCID 19711423, compound

HRID 725025Notes

Reaction equation

HRID 725025 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[C:10]([CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[CH:11]=[C:12]([CH2:14][CH2:15][NH:16][S:17]([CH2:20][C:21]([F:24])([F:23])[F:22])(=[O:19])=[O:18])[CH:13]=2)[CH:2]=1.N.C(O)(=O)C>Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[C:10]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:11]=[C:12]([CH2:14][CH2:15][NH:16][S:17]([CH2:20][C:21]([F:23])([F:24])[F:22])(=[O:18])=[O:19])[CH:13]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 19711420HCID 19711420, compound

Product 1

HCID 19711423HCID 19711423, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of ethyl 3-{3-(3-pyridylmethyl)-5-[2-(2,2,2-trifluoroethylsulphonylamino)ethyl]phenyl}propanoate (Example 10; 400 mg) in 6N hydrochloric acid (4.0 ml) was heated at 100° C. for 4 hours. The cool solution was basified with aqueous ammonia solution (SG 0.880) and then re-acidified by the dropwise addition of glacial acetic acid. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (MgSO4). Evaporation under vacuum of the solvent gave the title compound as a gum (265 mg); Rf 0.35 (SS 7). Found: C, 53.26; H, 4.78; N, 6.31. C19H21F3N2O4S requires C, 53.01; H, 4.92; N, 6.51%.

Workup

  1. extractionThe mixture was extracted several times with ethyl acetate
  2. washthe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customEvaporation under vacuum of the solvent

Sources & evidence

ORD record
ord-39d394b5308d4baa9c5cb4ccf124e7a8
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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