Trifluoroacetic acid → HCID 53766859, compound

HRID 862047Notes

Reaction equation

HRID 862047 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 cooled, 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. additionwas added
  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-f6b4e3358c4f4a4aa81bb57cb5e12ae4
Source dataset
uspto-grants-1998_02
Patent number
US05716980

Reaction notes

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