Water → HCID 59340064, compound

HRID 905914Notes

Reaction equation

HRID 905914 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:40])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:25]=[C:24]3[C:19]([C:20]([OH:39])=[C:21]([C:28]([NH:30][CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])=[O:29])[C:22](=[O:27])[N:23]3[CH3:26])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.O>ClCCl>[CH3:8][N:9]([CH3:40])[C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:25]=[C:24]3[C:19]([C:20]([OH:39])=[C:21]([C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[C:22](=[O:27])[N:23]3[CH3:26])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 59340041HCID 59340041, compound

Product 1

HCID 59340064HCID 59340064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.00 ml, 54 mmol) was added to a suspension of tert-butyl 2-(7-(4-(dimethylamino)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.057 g, 0.13 mmol) in dichloromethane (2.00 ml). After stirring at room temperature for 10 min water was added and the solution loaded in SCX MEGA BE column. The column was flushed with methanol extensible followed by 2M ammonia in methanol. The fractions obtained from the ammonia in methanol were collected and the solvent removed in vacuo. The residue was treated with 5N NaOH (2 ml) in THF (1 ml) and stirred at room temperature for 1 hour. The suspension was acidified with 5N HCl and the solids collected by filtration. The solids were washed with water, ether, dried in a vacuum oven at 50° C. to afford green solids (10 mg).

Workup

  1. additionwas added
  2. customThe column was flushed with methanol extensible

Sources & evidence

ORD record
ord-9c73ed0ee55c4a92bf2fd7bcab35cda8
Source dataset
uspto-grants-2011_09
Patent number
US08012968B2

Reaction notes

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