Trifluoroacetic acid → HCID 10617333, compound

HRID 2210063Notes

Reaction equation

HRID 2210063 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:21][CH2:22][C:23]([O:25][C:26](C)(C)[CH3:27])=[O:24])[CH:11]=[C:12]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=1)=[O:5])C.FC(F)(F)C(O)=O>ClCCl>[CH2:26]([O:25][C:23]([CH2:22][CH2:21][C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][C:4]([OH:5])=[O:3])[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10810955HCID 10810955, compound

Product 1

HCID 10617333HCID 10617333, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of t-butyl 3-[3-(2-ethoxycarbonylethyl)-5-(3-pyridyloxy)phenyl]propanoate (Preparation 29; 7.8 g) in dichloromethane (100 ml) was treated with trifluoroacetic acid (20 ml) and the resulting solution stirred at room temperature for 20 hours and then evaporated under vacuum. The residue was azeotroped twice with toluene, and then ether (ca 100 ml) and pyridine (ca 10 ml) were added sequentially. This mixture was washed with water and then the combined aqueous washings extracted with ethyl acetate. The organic solutions were combined, washed with water, dried (MgSO4) and evaporated under vacuum to provide an oil, which crystallised on trituration with an ether: hexane mixture to give the title compound (6.56 g), m.p. 85°-87° C. Found: C,66.67; H,6.04; N,3.90. C19H21NO5 requires C,66.46; H,6.16; N,4.08%.

Workup

  1. customevaporated under vacuum
  2. customThe residue was azeotroped twice with toluene
  3. additionether (ca 100 ml) and pyridine (ca 10 ml) were added sequentially
  4. washThis mixture was washed with water
  5. extractionthe combined aqueous washings extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated under vacuum
  9. customto provide an oil, which
  10. customcrystallised on trituration with an ether

Sources & evidence

ORD record
ord-567854d672f0485ab0465f7a80260c91
Source dataset
uspto-grants-1995_10
Patent number
US05457118

Reaction notes

Loading…