Trifluoroacetic acid → HCID 53766859, compound

HRID 1440405Notes

Reaction equation

HRID 1440405 reaction equation
C(OC([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([CH2:28][OH:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:8][C@H:9]([C:14]([NH:16][C@H:17]([CH2:28][OH:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53846502HCID 53846502, compound

Product 1

HCID 53766859HCID 53766859, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution, being ice cool, ed, of N-tert-butoxycarbonyl-(L)-isoleucyl-(L)-tryptophanol (1.0 g) in chloroform (10 ml), trifluoroacetic acid (5%, 0.5 g) was added, followed by stirring at the same temperature for 4 hours. After the reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue. The ethyl acetate layer was washed with water and dried (MgSO4), and the solvent was distilled off to yield (L)-isoleucyl-(L)-tryptophanol as an oily substance. This oily substance was dissolved in chloroform (20 ml), and p-toluenesulfonyl chloride (0.52 g) was added and then triethylamine (1.4 ml) was added at 0° C. After stirring at room temperature for 2 days, the reaction mixture was poured over water and extracted with chloroform. After the chloroform layer was dried (MgSO4), the solvent was distilled off, and the oily residue was recrystallized from ethyl acetate to yield N-(p-toluenesulfonyl)-(L)-isoleucyl-(L)-tryptophanol (0.32 g, 28%).

Workup

  1. temperaturecool
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-701eb29eaa554a74901015a60347af94
Source dataset
uspto-grants-1996_03
Patent number
US05498728

Reaction notes

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