Trifluoroacetic acid → HCID 16736227, compound

HRID 386438Notes

Reaction equation

HRID 386438 reaction equation
[O:1]=[C:2]([C:25]1[O:26][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:28][N:29]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)C(=O)OC(C)(C)C)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]=[C:2]([C:25]1[O:26][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:28][N:29]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67529312HCID 67529312, compound

Product 1

HCID 16736227HCID 16736227, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 4-(3-oxo-3-(5-(pyridin-2-yl)oxazol-2-yl)propyl)phenyl-(phenyl)carbamate (S36, 26 mg, 0.055 mmol) in anhydrous CH2Cl2 (0.8 mL) was treated with TFA (0.2 mL) and was stirred for 1 h at 0° C. The reaction mixture was allowed to warm at 25° C. and was stirred for 2 h. The reaction mixture was concentrated, diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. Column chromatography (SiO2, 1×3 cm, pretreated with 1% Et3N-hexanes, 10-25% EtOAc-hexanes gradient) afforded 11g (14 mg, 0.038 mmol, 70%) as a pale yellow solid: 1H NMR (CDCl3, 500 MHz) 8.67 (app d, 1H, J=4.0 Hz), 7.89-7.86 (m, 2H), 7.81 (td, 1H, J=7.7, 1.8 Hz), 7.33-7.31 (m, 1H), 7.25 (dd, 2H, J=8.4, 7.3 Hz), 7.18 (d, 2H, J=8.4 Hz), 7.04-7.01 (m, 4H), 6.90 (t, 1H, J=7.3 Hz), 5.68 (br s, 1H), 3.45 (t, 2H, J=7.7 Hz), 3.07 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 150 MHz) 187.5, 157.3, 153.3, 150.1, 146.3, 143.5, 141.3, 137.1, 133.1, 129.3 (2C), 126.9, 124.1, 120.6, 120.4, 118.4, 117.3, 40.9, 29.1, 28.2; IR (film) νmax 3389, 3053, 2925, 1698, 1598, 1519, 1495, 1469, 1425, 1380, 1311, 1176, 1152, 1118, 1064, 991, 911, 784, 738, 694 cm−1; ESI-TOF m/z 369.1475 (C23H19N3O2+ requires 369.1477).

Workup

  1. temperatureto warm at 25° C.
  2. stirringwas stirred for 2 h
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with saturated aqueous NaHCO3
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2505fc13049a45438e2f6f1be90f45ea
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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