Trifluoroacetic acid → HCID 58093190, compound

HRID 1805750Notes

Reaction equation

HRID 1805750 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([Cl:18])[N:12]=[C:11]([Cl:19])[C:10]=1[C:20]([O:22]C(C)(C)C)=[O:21]>ClCCl>[NH2:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([Cl:18])[N:12]=[C:11]([Cl:19])[C:10]=1[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58093078HCID 58093078, compound

Product 1

HCID 58093190HCID 58093190, 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).

Sources & evidence

ORD record
ord-51227ef23545476a9fca4653edbe844d
Source dataset
uspto-grants-2013_01
Patent number
US08354526B2

Reaction notes

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