Trifluoroacetic acid → HCID 57848904, compound

HRID 736806Notes

Reaction equation

HRID 736806 reaction equation
C([O:5][NH:6][C:7]([C@:9]1([CH3:44])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]([S:38]([CH:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])[CH2:10]1)=[O:8])(C)(C)C.FC(F)(F)C(O)=O>>[OH:5][NH:6][C:7]([C@:9]1([CH3:44])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:17])=[O:18])[CH2:13][CH2:12][N:11]([S:38]([CH:41]([CH3:42])[CH3:43])(=[O:40])=[O:39])[CH2:10]1)=[O:8]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86607903HCID 86607903, compound

Product 1

HCID 57848904HCID 57848904, compoundYield 90.6%

Conditions

Temperature
45 °C

Procedure

To 0.11 g of (3S,4R)-N-tert-butoxy-1-(isopropylsulfonyl)-3-methyl-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-3-carboxamide was added 3 mL of trifluoroacetic acid and the resulting mixture was stirred at 45° C. for 8 h. The reaction mixture was then concentrated and the residue was purified by silica chromatography (silica prewashed with MeOH) eluting with a gradient of 5-20% MeOH/CH2Cl2 to afford (3S,4R)-N-hydroxy-1-(isopropylsulfonyl)-3-methyl-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-3-carboxamide (0.091 g, 83%) as a colorless solid. MS: 591.2 (M+H)+

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by silica chromatography (silica prewashed with MeOH)
  3. washeluting with a gradient of 5-20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-80124c58e1e04f70a458ec5152acb0e6
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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