Trifluoroacetic acid → (6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylic acid

HRID 2240502Notes

Reaction equation

HRID 2240502 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]1[C@H:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=[C:30]([CH3:38])[CH:29]=3)=[CH:22][CH:21]=2)=[O:18])[C@@H:15]([C:39]([O:41]C(C)(C)C)=[O:40])[CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10]1>C(Cl)Cl>[CH3:8][N:9]1[C@H:16]([C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=[C:30]([CH3:38])[CH:29]=3)=[CH:24][CH:25]=2)=[O:18])[C@@H:15]([C:39]([OH:41])=[O:40])[CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67007475tert-butyl (6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylate

Product 1

HCID 67006214(6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylic acidYield 149.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.0 mL) was added to a solution of tert-butyl(6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylate (105.0 mg) in CH2Cl2 (1.0 mL) and the mixture was stirred at room temperature for 5 h. The solvent was removed to provide (6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylic acid (140 mg) as an TFA salt. ESI (M+H)+460.3.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-31de17144706428fa2e369f064ba24f3
Source dataset
uspto-grants-2010_05
Patent number
US07723349B2

Reaction notes

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