Trifluoroacetic acid → HCID 67500750, compound

HRID 1919829Notes

Reaction equation

HRID 1919829 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

Sources & evidence

ORD record
ord-79a34e5395ea41b9a85ba2dec9b8893b
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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