Hydrochloric Acid → HCID 68817278, compound

HRID 736740Notes

Reaction equation

HRID 736740 reaction equation
C[O:2][C:3]([CH:5]1[CH:10]([N:11]([CH3:34])[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>[CH3:34][N:11]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[C:25]([CH3:33])[CH:24]=2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])[CH:10]1[CH2:9][CH2:8][O:7][CH2:6][CH:5]1[C:3]([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68818589HCID 68818589, compound

Product 1

HCID 68817278HCID 68817278, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid methyl ester (0.2 g, 0.41 mmol) and lithium hydroxide (0.148 g, 4.1 mmol) in THF:methanol:H2O (2.5: 1.5:1.5 mL) was stirred at 25° C. for 19 h. The solution was then 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 produce 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid as a crude solid (0.120 g, 63%). 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-60181999fdc541e68b19f56df961ea5f
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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