Trifluoroacetic acid → HCID 178471612, compound

HRID 852862Notes

Reaction equation

HRID 852862 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH:5]=[CH:6][CH:7]([NH:33]C(OC(C)(C)C)=O)[CH2:8][C:9]1[N:10]=[CH:11][N:12](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=1)[CH3:2].C(O)(C(F)(F)F)=O>>[CH2:1]([O:3][C:4](=[O:41])[CH:5]=[CH:6][CH:7]([NH2:33])[CH2:8][C:9]1[N:10]=[CH:11][NH:12][CH:13]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 694162234-tert-Butoxycarbonylamino-5-(1-trityl-1H-imidazol-4-yl)-pent-2-enoic acid ethyl ester

Product 1

HCID 178471612HCID 178471612, compoundYield 53%

Procedure

A representative procedure is as follows. 4-tert-Butoxycarbonylamino-5-(1-trityl-1H-imidazol-4-yl)-pent-2-enoic acid ethyl ester (100 mg, 0.181 mmol) was stirred with TFA (5 mL) overnight under an atmosphere of argon. The TFA was removed and the residue triturated with Et2O. The remaining solid was subject to preparative reverse phase HPLC (30% B to 100% B over 20 min) to yield after lyophilization a gum (20 mg, 53%). 1H NMR (300 MHz, d6-DMSO) δ 1.19 (3H, t, J=7.02), 3.19 (2H, br s), 4.12 (2H, q, J=7.02), 4.33 (1H, m), 6.09 (1H, d, J=15.87), 6.76 (1H, dd, J=7.14, 15.87), 7.49 (1H, br s), 9.01 (1H, br s). 13C NMR (d6-DMSO) δ 164.76, 141.83, 134.64, 127.39, 125.08, 118.09, 60.58, 50.03, 27.57, 14.06.

Workup

  1. customThe TFA was removed
  2. customthe residue triturated with Et2O
  3. customwas subject to preparative reverse phase HPLC (30% B to 100% B over 20 min)

Sources & evidence

ORD record
ord-27124b55238d4ea281bf2ea94a942cda
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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