Trifluoroacetic acid → HCID 15896051, compound

HRID 376910Notes

Reaction equation

HRID 376910 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][N:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:19]([N:8]([CH2:7][C:6]([OH:27])=[O:5])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15896050HCID 15896050, compound

Product 1

HCID 15896051HCID 15896051, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An ice-cooled solution of [octyl-(toluene-4-sulfonyl)amino]-acetic acid tert-butyl ester (5.2 g, 0.013 mol) in dichloromethane (50 ml) was further diluted by the addition of 25% TFA in dichloromethane (200 ml). The reaction mixture was stored at 4° C. overnight. Solvents were removed under reduced pressure and the residue was azeotroped with toluene. The resulting crude oil was purified by flash chromatography (silica gel, 10% methanol in dichloromethane) to give the title compound as a white solid (4.4 g, 99%). 1H NMR: δ (CDCl3), 9.77 (1H, br s), 7.71 2H, d, J=8.3 Hz), 7.25 (2H, d, J=8.2 Hz), 4.00 (2H, br s), 3.19 (2H, dd, J=7.4, 7.7 Hz), 2.38 (3H, s), 1.50-1.30 (2H, m), 1.30-1.05 (10H, m) and 0.85 (3H, t, J=6.6 Hz).

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue was azeotroped with toluene
  3. customThe resulting crude oil was purified by flash chromatography (silica gel, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8b34daa50126426586dc2c9a247fdc29
Source dataset
uspto-grants-2000_02
Patent number
US06022898

Reaction notes

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