Trifluoromethanesulfonic acid → Phenylalanine amide

HRID 1079300Notes

Reaction equation

HRID 1079300 reaction equation
[NH:1](C(C1C=CC=CC=1)=O)[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.COC1C=C(OC)C=CC=1C[NH-:26].FC(F)(F)S(O)(=O)=O>FC(F)(F)C(O)=O>[NH2:1][C@H:2]([C:10]([NH2:26])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 131719731HCID 131719731, compound

Product 1

HCID 445694Phenylalanine amide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Bz-Phe-2,4-dimethoxybenzylamide (4.2 mg) was dissolved in trifluoroacetic acid (1.0 ml) containing 10% (v/v) trifluoromethane sulfonic acid (TFMSA) and the reaction mixture was kept in the dark for 1 h at 20° C. TFA/TFMSA was removed by blowing with N2 and the residue was suspended in 95% (v/v) CH3CN (1.0 ml). The reaction mixture was analyzed by HPLC system-7 and the generated Bz-Phe-NH2 (>95%) was determined quantitatively using a Bz-Phe-NH2 standard solution (Bz-Phe-NH2 was purchased from Bachem, Switzerland).

Workup

  1. customdark for 1 h
  2. customat 20° C
  3. customTFA/TFMSA was removed

Sources & evidence

ORD record
ord-48909c2becb74d0aa492fe514b384ec9
Source dataset
uspto-grants-1996_12
Patent number
US05580751

Reaction notes

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