Trifluoroacetic acid → HCID 178461862, compound

HRID 980227Notes

Reaction equation

HRID 980227 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C@H:16]([NH:18]C(=O)OC(C)(C)C)[CH3:17])[C:3]=1[C:26]([NH:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1)=[O:27].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:18][C@@H:16]([C:4]1[C:3]([C:26]([NH:28][C:29]2[S:30][CH:31]=[CH:32][N:33]=2)=[O:27])=[C:2]([OH:1])[C:11]2[C:6](=[C:7]([C:12]([F:13])([F:15])[F:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178462195HCID 178462195, compound

Product 1

HCID 178461862HCID 178461862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7 g of the product of Example 3 were suspended in 140 ml of methylene chloride and 70 ml of trifluoroacetic acid were slowly added with the temperature falling to 15° C. Contact was maintained for 4 hours and then, after concentrating to dryness under reduced pressure, the residue was taken up in 100 ml of ether. The crystals were separated by filtration and the product was slowly added to 50 ml of a 10% aqueous solution of sodium bicarbonate. After stirring, filtration, and washing with water, the crude product was treated at reflux with 300 ml of methanol without complete solution and after cooling and concentrating to 50 ml, 2.3 g of 2-[(R) 1-aminoethyl]-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 265° C. and with a specific rotation of [α]D =-72°±2.5° (c=0.5% in CH3COOH) were obtained.

Workup

  1. customfalling to 15° C
  2. temperatureContact was maintained for 4 hours
  3. concentrationafter concentrating to dryness under reduced pressure
  4. customThe crystals were separated by filtration
  5. additionthe product was slowly added to 50 ml of a 10% aqueous solution of sodium bicarbonate
  6. filtrationfiltration
  7. washwashing with water
  8. additionthe crude product was treated
  9. temperatureat reflux with 300 ml of methanol without complete solution
  10. temperatureafter cooling
  11. concentrationconcentrating to 50 ml, 2.3 g of 2-[(R) 1-aminoethyl]-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 265° C. and with a specific rotation of [α]D =-72°±2.5° (c=0.5% in CH3COOH)
  12. customwere obtained

Sources & evidence

ORD record
ord-4be173969fad4acfaeb1fad3b4dd0db9
Source dataset
uspto-grants-1987_01
Patent number
US04636512

Reaction notes

Loading…