Trifluoroacetic acid → HCID 67500750, compound

HRID 1436343Notes

Reaction equation

HRID 1436343 reaction equation
[CH3:1][O:2][C@@H:3]([CH3:22])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([NH:14]C(=O)OC(C)(C)C)[CH3:13])=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C@@H:3]([CH3:22])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([NH2:14])[CH3:13])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86621592HCID 86621592, compound

Product 1

HCID 67500750HCID 67500750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [1-(4-{[(2S)-2-methoxypropyl]oxy}phenyl)ethyl]carbamate (0.29 g, 0.94 mmol) was treated with trifluoroacetic acid (2 mL) in dichloromethane (18 mL) for 25 minutes, the volatiles removed under reduced pressure and the residue purified by silica gel column chromatography using dichloromethane:methanol:triethylamine 98:1:1 giving the title compound in 0.12 g (59%) yield 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (s, 2 H) 7.34-7.41 (m, J=8.78 Hz, 2 H) 6.97-7.03 (m, 2 H) 4.35 (q, J=6.78 Hz, 1 H) 3.93 (d, J=5.02 Hz, 2 H) 3.60-3.70 (m, 1 H) 3.30 (s, 3 H) 2.96 (q, J=7.11 Hz, 1 H) 1.45 (d, J=6.78 Hz, 3 H) 1.16 (d, J=6.27 Hz, 3 H)

Workup

  1. customthe volatiles removed under reduced pressure
  2. customthe residue purified by silica gel column chromatography
  3. customyield 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (s, 2 H) 7.34-7.41 (m, J=8.78 Hz, 2 H) 6.97-7.03 (m, 2 H) 4.35 (q, J=6.78 Hz, 1 H) 3.93 (d, J=5.02 Hz, 2 H) 3.60-3.70 (m, 1 H) 3.30 (s, 3 H) 2.96 (q, J=7.11 Hz, 1 H) 1.45 (d, J=6.78 Hz, 3 H) 1.16 (d, J=6.27 Hz, 3 H)

Sources & evidence

ORD record
ord-0cff778be1fd4254b6f16a3a174f7196
Source dataset
uspto-grants-2009_11
Patent number
US07618993B2

Reaction notes

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