Trifluoroacetic acid → (R)-methyl 1-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1530767Notes

Reaction equation

HRID 1530767 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:18])[C@H:5]([NH:13][C:14]([O:16][CH3:17])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.FC(F)(F)C(O)=O.FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C(I)C=CC=1)=O>ClCCl>[CH3:1][O:2][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@@H:5]([NH:13][C:14](=[O:15])[O:16][CH3:17])[C:4]1=[O:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10682227(R)-methyl 1-(methoxyamino)-1-oxo-3-phenylpropan-2-ylcarbamateHCID 12041285Bistrifluoroacetoxyiodobenzene

Product 1

HCID 10538623(R)-methyl 1-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (R)-N-methoxy-2-(methoxycarbonylamino)-3-phenylpropanamide (III, EXAMPLE 2, 11.25 g, 44.6 mmol) in dichloromethane (170 ml) is cooled in an ice bath and trifluoroacetic acid (9.25 ml, 13.7 g, 0.120 mol) is added. Bis(trifluoroacetoxy)iodobenzene (19.78 g, 0.046 mol) is added portion wise over 10 min at 0°, and the mixture is stirred at this temperature for one hour. The mixture is washed with sodium carbonate mixture (10%) and dried over magnesium sulfate. The solvent is removed under reduced pressure to give a concentrate. Purification by flash chromatography (230-400 mesh silica gel, 40-50% ethyl acetate/hexane) gives the desired product. An analytical sample is crystallized from ethyl acetate/hexane to give the title compound, mp=117-119°; NMR (CDCl3) 2.85, 3.44, 3.72, 3.93, 4.42, 5.82, 7.09, 7.33 and 7.22 δ; IR (mineral oil) 1722 and 1703 cm−1; [a]25D=+34.20 (CH3OH, c=0.927).

Workup

  1. temperatureis cooled in an ice bath
  2. washThe mixture is washed with sodium carbonate mixture (10%)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customto give a concentrate
  6. customPurification by flash chromatography (230-400 mesh silica gel, 40-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-850a37c00bba4334bb5aa9b1f9dccc8f
Source dataset
uspto-grants-2001_03
Patent number
US06197339B1

Reaction notes

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