Trifluoroacetic acid → HCID 58093078, compound

HRID 1805749Notes

Reaction equation

HRID 1805749 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([Cl:26])=[N:10][C:11]([Cl:25])=[C:12]([C:16]=1[NH:17]C(OC(C)(C)C)=O)[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[NH2:17][C:16]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([Cl:25])[N:10]=[C:9]([Cl:26])[C:8]=1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58092982HCID 58092982, compound

Product 1

HCID 58093078HCID 58093078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In scheme (V), 5-(tert-butoxycarbonyl)-4-(tert-butoxycarbonylamino)-2,6-dichloronicotinic acid (4) is first treated with 25% trifluoracetic acid (TFA) in dichloromethane (DCM) at room temperature (25° C.) for 2 hours, removing one of the two Boc groups and forming 4-amino-5-(tert-butoxycarbonyl)-2,6-dichloronicotinic acid (5). A stronger condition (reflux at 60° C., 25% TFA in DCM, 2 h) is then used to maximize hydrolysis of the tert-butyl ester of 4-amino-5-(tert-butoxycarbonyl)-2,6-dichloronicotinic acid (5) and obtain 4-amino-2,6-dichloropyridine-3,5-dicarboxylic acid (6).

Workup

  1. customremoving one of the two Boc groups

Sources & evidence

ORD record
ord-448a4c8916b54a07bbb3d3788380ad72
Source dataset
uspto-grants-2013_01
Patent number
US08354526B2

Reaction notes

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