Trifluoroacetic acid → HCID 7272330, compound

HRID 2096107Notes

Reaction equation

HRID 2096107 reaction equation
[NH:1]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C@H:2]([C:10]([NH:12][C@H:13]([C:18]([O:20]C(C)(C)C)=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>O>[NH:1]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C@H:2]([C:10]([NH:12][C@H:13]([C:18]([OH:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13818605HCID 13818605, compound

Product 1

HCID 7272330HCID 7272330, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg Z-Phe-Leu-OtBu was added to 5 mL CF3COOH to which a drop of water had been added. The mixture was stirred for 2 h at ambient temperature, concentrated in vacuo and co-evaporated with 10 mL toluene (2×) to obtain Z-Phe-Leu-OH in quantitative yield. 1H-NMR (CDCl3, 300 MHz): δ 7.31-7.04 (m, 10H), 6.82 (d, 1H, J=6.6 Hz), 5.79 (d, 1H, J=7.3 Hz), 4.93 (s, 2H), 4.44 (m, 2H), 2.94 (m, 2H), 1.51 (m, 3H), 0.77 (m, 6H).

Workup

  1. additionhad been added
  2. concentrationconcentrated in vacuo and co-evaporated with 10 mL toluene (2×)

Sources & evidence

ORD record
ord-9830b11954074b3e926b98523cd27160
Source dataset
uspto-grants-2013_05
Patent number
US08450084B2

Reaction notes

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