Hydrochloric Acid → 4-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid

HRID 736737Notes

Reaction equation

HRID 736737 reaction equation
C[O:2][C:3]([CH:5]1[CH:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9][CH2:8][O:7][CH2:6]1)=[O:4].[OH-].[Li+].Cl>C1COCC1.CO.O.C(OCC)(=O)C>[CH3:33][C:25]1[CH:24]=[C:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([S:12]([NH:11][CH:10]3[CH2:9][CH2:8][O:7][CH2:6][CH:5]3[C:3]([OH:4])=[O:2])(=[O:13])=[O:14])=[CH:16][CH:17]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 688172194-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester

Product 1

HCID 688206984-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester (0.3 g, 0.64 mmol) and lithium hydroxide (0.153 g, 6.38 mmol) in THF:methanol:H2O (2.5: 1.5:1.5 mL) was stirred at 25° C. for 19 h. The solution was diluted with ethyl acetate (2×30 mL) and the aqueous layer was acidified with 2N HCl to pH ˜2. The aqueous layer was washed with ethyl acetate (3×40 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to provide 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid as a crude solid (0.280 g, 97%). MS: 457 (M+H)+.

Workup

  1. washThe aqueous layer was washed with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-adeaba9e308c4a3ebf27e3d670008c4b
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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