Trifluoroacetic acid → HCID 86689985, compound

HRID 1754052Notes

Reaction equation

HRID 1754052 reaction equation
[CH3:1][S:2]([CH2:4][CH2:5][CH:6]([NH:18]C(=O)OC(C)(C)C)[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:8])=[O:3].C(O)(C(F)(F)F)=O>ClCCl>[NH2:18][CH:6]([CH2:5][CH2:4][S:2]([CH3:1])=[O:3])[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86689984HCID 86689984, compound

Product 1

HCID 86689985HCID 86689985, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4-(methylsulfinyl)-1-(octylamino)-1-oxobutan-2-yl)carbamate (6.43 g, 17.1 mmol) in dichloromethane (65 mL) at 0° C. was added TFA (65 mL) and the ice bath was removed. After stirring for 1 hour the reaction was concentrated to give an oil. The oil was purified by silica gel chromatography with 0-10% methanol/dichloromethane (with 15% ammonium hydroxide additive in methanol) to give a white solid (4.5 g, 95%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.87 (t, J=6.83 Hz, 3 H) 1.19-1.33 (m, 10 H) 1.36-1.47 (m, 2 H) 1.61-1.78 (m, 1 H) 1.84-1.99 (m, 1 H) 2.17-2.38 (m, 1 H) 2.52 (s, 3 H) 2.61-2.72 (m, 1 H) 2.75-2.84 (m, 1 H) 2.99-3.13 (m, 2 H) 3.19-3.29 (m, 1 H) 3.28-3.46 (m, 1 H) 7.89 (br. s., 1 H). m/z 277 (MH+).

Workup

  1. customthe ice bath was removed
  2. concentrationwas concentrated
  3. customto give an oil
  4. customThe oil was purified by silica gel chromatography with 0-10% methanol/dichloromethane (with 15% ammonium hydroxide additive in methanol)

Sources & evidence

ORD record
ord-a617a8a7cfdf4fdfa9ab28ba381d1322
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

Loading…