Trifluoroacetic acid → HCID 131731088, compound

HRID 1912374Notes

Reaction equation

HRID 1912374 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:19]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>CO>[NH2:1][C@H:2]([C:19]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731087HCID 131731087, compound

Product 1

HCID 131731088HCID 131731088, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cbz-Phe (4-CH2NHBoc)-Leu-OMe 79 (282 mg, 508 μmol) was dissolved in MeOH. TFA (45 μl, 607 μmol, 1.2 equiv.) was added and the mixture was bubbled through with Ar for 20 minutes. 10% Pd/C was added (50 mg) and the flask was filled with an H2 atmosphere for 3 hours. The mixture was filtered over CELITE and concentrated. The residue was dissolved in DCM and sat. aq. NaHCO3 and the aqueous layer was extracted with DCM (3×). The organic layers were dried over Na2SO4 and concentrated to yield the title compound (221 mg, quant.), which was used without further purification. 1H NMR (400 MHz, CDCl3): δ ppm 7.67 (d, J=8.6 Hz, 1H), 7.22 (d, J=8.0 Hz, 2H), 7.17 (d, J=8.1 Hz, 2H), 5.11 (s, 1H), 4.61 (td, J=8.9, 5.0 Hz, 1H), 4.28 (d, J=5.6 Hz, 2H), 3.72 (s, 3H), 3.61 (dd, J=9.0, 4.0 Hz, 1H), 3.19 (dd, J=13.7, 3.9 Hz, 1H), 2.72 (dd, J=13.7, 9.0 Hz, 1H), 1.70-1.48 (m, 3H), 1.45 (s, 9H), 1.03-0.89 (m, 6H). 13C NMR (101 MHz, CDCl3): δ ppm 173.91, 173.25, 155.77, 137.47, 136.49, 129.35, 127.56, 79.21, 56.06, 52.03, 50.13, 44.07, 41.22, 40.26, 28.23, 24.64, 22.69, 21.68.

Workup

  1. customthe mixture was bubbled through with Ar for 20 minutes
  2. addition10% Pd/C was added (50 mg)
  3. additionthe flask was filled with an H2 atmosphere for 3 hours
  4. filtrationThe mixture was filtered over CELITE
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM
  7. extractionsat. aq. NaHCO3 and the aqueous layer was extracted with DCM (3×)
  8. dry with materialThe organic layers were dried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-70c6567bb2c747e7abdec0f2478cdcbb
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

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