Trifluoroacetic acid → HCID 10733906, compound

HRID 725036Notes

Reaction equation

HRID 725036 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:14]=[C:15]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:14]=[C:15]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 10621626HCID 10621626, compound

Product 1

HCID 10733906HCID 10733906, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-[3-(2-t-butoxycarbonylaminoethyl)-5(3-pyridylmethyl)phenyl]propanoate (Preparation 39; 4.10 g) and trifluoroacetic acid (4.1 ml) in dry dichloromethane (41 ml) was stirred for 6 hours, additional 4.1 ml portions of trifluoroacetic acid being added after 2 and 5 hours. The solution was evaporated under vacuum and the residue basified with aqueous sodium bicarbonate solution. The mixture was extracted several times with dichloromethane and the combined extracts were dried (MgSO4) and evaporated under vacuum. Water (ca 75 ml) was added and this mixture was acidified to pH 4 with glacial acetic acid and then extracted several times with ethyl acetate. The aqueous layer was basified with aqueous ammonia solution (SG 0.880) and extracted several times with dichloromethane. The combined dichloromethane extracts were washed with water, dried (MgSO4) and evaporated under vacuum to give the title compound as an oil (2.24 g); Rf 0.10 (SS 2); δ (CDCl3): 1.07(2H,br), 1.20(3H,t,J=7.1 Hz), 2.56(2H,t,J=7.8 Hz), 2.66(2H,t,J=6.9 Hz), 2.85-2.93(4H,m), 3.90(2H,s), 4.09(2H,q,J=7.1 Hz), 6.84 (2H,s), 6.88(1H,s), 7.16-7.20(1H,m), 7.43(1H,d,J=7.8 Hz), 8.43-8.47(2H,m).

Workup

  1. customThe solution was evaporated under vacuum
  2. extractionThe mixture was extracted several times with dichloromethane
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. customevaporated under vacuum
  5. additionWater (ca 75 ml) was added
  6. extractionextracted several times with ethyl acetate
  7. extractionextracted several times with dichloromethane
  8. washThe combined dichloromethane extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-3ba3577d6ced43239acd10f5a8edf215
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

Loading…