Trifluoroacetic acid → HCID 86741803, compound

HRID 1252837Notes

Reaction equation

HRID 1252837 reaction equation
C(OC(=O)[C@@H]1CCCN1CCCSC(=O)[C@H](CC1C=CC=CC=1C(=O)C1C=CC=CC=1)N)(C)(C)C.C([O:40][C:41](=[O:71])[C@@H:42]1[CH2:46][CH2:45][CH2:44][N:43]1[C:47](=[O:70])[CH2:48][CH2:49][S:50][C:51](=[O:69])[C@H:52]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61](=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[NH2:53])(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:61]([C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=1[CH2:54][C@@H:52]([C:51]([S:50][CH2:49][CH2:48][C:47]([N:43]1[CH2:44][CH2:45][CH2:46][C@H:42]1[C:41]([OH:71])=[O:40])=[O:70])=[O:69])[NH2:53])(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18609848HCID 18609848, compoundHCID 86741804HCID 86741804, compound

Product 1

HCID 86741803HCID 86741803, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

The product of step (b), N-(2-benzoylphenylalanylthiopropanoyl)-L-proline-t-butyl ester, 1.25 g, was suspended in 4 ml anisole and reacted with 8 ml trifluoroacetic acid for 1 hour at room temperature with stirring. In view of the fact that some starting material was later recovered, the reaction time should be increased. Trifluoroacetic acid was removed with a rotary evaporator under high vacuum. The residue was dissolved in 1 ml THF and chromatographed on a 2.2 cm×99 cm column of Sephadex LH-20 eluted with THF. Fractions of about 5.3 ml were collected. The product was eluted in fractions 41-43. The combined fractions41-43 were evaporated to dryness, dissolved in a small amount of isopropanol and rechromatographed on a 1.2 cm×95 cm LH-20 column, eluted with isopropanol. Fractions of about 2.05 ml were collected. Fractions 48-50 contained 78 mg of the desired compound as an oil. Side fractions 46-47 and 51-53 were saved for rechromatography. The oil was dissolved in a small volume of THF in a vial, then the THF was evaporated under a stream of N2. The vial was then placed in a round bottom flask connected to a rotary evaporator. After 3 hours under high vacuum, a stable, dry foam was obtained.

Workup

  1. customIn view of the fact that some starting material was later recovered
  2. temperaturethe reaction time should be increased
  3. customTrifluoroacetic acid was removed with a rotary evaporator under high vacuum
  4. dissolutionThe residue was dissolved in 1 ml THF
  5. customchromatographed on a 2.2 cm×99 cm column of Sephadex
  6. washeluted with THF
  7. customFractions of about 5.3 ml were collected
  8. washThe product was eluted in fractions 41-43
  9. customThe combined fractions41-43 were evaporated to dryness
  10. dissolutiondissolved in a small amount of isopropanol
  11. customrechromatographed on a 1.2 cm×95 cm LH-20 column
  12. washeluted with isopropanol
  13. customFractions of about 2.05 ml were collected
  14. dissolutionThe oil was dissolved in a small volume of THF in a vial, then the THF
  15. customwas evaporated under a stream of N2
  16. customThe vial was then placed in a round bottom flask
  17. customconnected to a rotary evaporator
  18. customa stable, dry foam
  19. customwas obtained

Sources & evidence

ORD record
ord-4e598b2ab1434ca5b234d3c07d1a8df2
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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