(3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide → (3R,4R)-N-hydroxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide

HRID 736788Notes

Reaction equation

HRID 736788 reaction equation
C([O:5][NH:6][C:7]([C@:9]1([CH3:38])[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][O:11][CH2:10]1)=[O:8])(C)(C)C>FC(F)(F)C(O)=O>[OH:5][NH:6][C:7]([C@:9]1([CH3:38])[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][O:11][CH2:10]1)=[O:8]

Participants

3

Reactant 1

HCID 86607888(3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide

Product 1

HCID 11856141(3R,4R)-N-hydroxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The (3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide (0.52 g, 0.96 mmol) from Step 10 was stirred in neat trifluoroacetic acid (3 mL) at 40° C. for 3.5 h. The reaction mixture was then concentrated in vacuo and chased with methanol. The residue was then stirred in ethyl acetate (100 mL) and saturated NaHCO3 (50 mL) for 15 min. The organic layer was washed with water (50 mL), then with brine (50 mL), dried over MgSO4, and concentrated. The residue was purified by chromatography on silica eluting with 5-8% MeOH/CH2Cl2 to yield 140 mg (30%) of (3R,4R)-N-hydroxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide as an off-white solid. In addition, 35% of the starting material was recovered. HRMS: calcd for C24H27N3O6S+H+, 486.16933; found (ESI-FT-MS, [M+H]+1), 486.1695

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo and chased with methanol
  2. washThe organic layer was washed with water (50 mL)
  3. dry with materialwith brine (50 mL), dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica eluting with 5-8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a0e920e55a94424d8f17010fa6a047d7
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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