Pyridine → HCID 19741703, compound

HRID 2255120Notes

Reaction equation

HRID 2255120 reaction equation
O=[CH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][C:5]=1[O:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].[N:33]1C=CC=CC=1.FC(F)(F)C(ONC(=O)C(F)(F)F)=O>C1(C)C=CC=CC=1>[C:2]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][C:5]=1[O:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26])#[N:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69634(2,2,2-Trifluoroacetyl)azanyl 2,2,2-trifluoroacetateHCID 19741713HCID 19741713, compound

Product 1

HCID 19741703HCID 19741703, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 4-(2-oxoethyl)-α-[(phenylcarbonyl)amino]-3-[(phenylcarbonyl)oxy]benzeneacetate from Preparation 9 above in toluene containing pyridine (2.3 eq) is treated with O,N-bistrifluoroacetyl hydroxyl amine (1.0 eq). The resulting solution is allowed to stir until no starting material remains. The reaction mixture is washed with saturated eq NaHCO3 solution, dried (MgSO4), and concentrated. The product of the formula 15 above is purified by silica gel chromatography.

Workup

  1. washThe reaction mixture is washed with saturated eq NaHCO3 solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe product of the formula 15 above is purified by silica gel chromatography

Sources & evidence

ORD record
ord-b94d725e9c77466a896070276ef6aacd
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

Loading…