Trifluoroacetic acid → (S)-2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetic Acid

HRID 2388672Notes

Reaction equation

HRID 2388672 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[CH2:23][O:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])(=[O:12])=[O:11])=[C:5]([CH3:33])[CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[CH2:23][O:24][CH2:25][C:26]([OH:28])=[O:27])(=[O:12])=[O:11])=[C:5]([CH3:33])[CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57916258(S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetate

Product 1

HCID 46222615(S)-2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinoline-2-yl)methoxy)acetate (1 g, 2.103 mmol) was dissolved in dichloromethane (15 ml) and trifluoroacetic acid (3.24 ml, 42.05 mmol) was added slowly. After stirring at room temperature for 2 h, the solvent was removed in vacuo and the residue was co-evaporated twice more with 20 ml of toluene each time. Yield: 0.84 g (95%).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6c86a55d2675473baebc7dbe39a9ca0d
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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