Trifluoroacetic acid → HCID 86607902, compound

HRID 736804Notes

Reaction equation

C([O:5][NH:6][C:7]([C@:9]1([CH3:40])[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]([CH:38]=[O:39])[CH2:10]1)=[O:8])(C)(C)C.FC(F)(F)C(O)=O>>[CH:38]([N:11]1[CH2:12][CH2:13][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])[C@@:9]([CH3:40])([C:7]([NH:6][OH:5])=[O:8])[CH2:10]1)=[O:39]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 57848919HCID 57848919, compound

Product 1

HCID 86607902HCID 86607902, compoundYield 60.3%

Conditions

Temperature: 45 °C

Procedure

To 0.092 g of (3S,4R)-N-tert-butoxy-1-formyl-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide was added 3 mL of trifluoroacetic acid, and the resulting mixture was stirred at 45° C. for 8 h, and then concentrated. The residue was purified by silica chromatography (silica pre-washed with MeOH), eluting with a gradient of 5-20% MeOH/CH2Cl2 to afford (3S,4R)-1-formyl -N-hydroxy-3-methyl-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-3-carboxamide (0.05 g, 60%) as a colorless solid. MS: 513.2 (M+H)+

Workup

concentrationconcentrated
customThe residue was purified by silica chromatography (silica pre-washed with MeOH)
washeluting with a gradient of 5-20% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-fb1625b2d2344d3d92636cdf35e7521c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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