Lithium Hydroxide → HCID 68818793, compound

HRID 736746Notes

Reaction equation

HRID 736746 reaction equation
C[O:2][C:3]([CH:5]1[CH:9]([N:10]([CH3:33])[S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:8][O:7][CH2:6]1)=[O:4].[OH-].[Li+]>C1COCC1.CO.O>[CH3:33][N:10]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([CH3:32])[CH:23]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:13])[CH:9]1[CH2:8][O:7][CH2:6][CH:5]1[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68818472HCID 68818472, compound

Product 1

HCID 68818793HCID 68818793, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-furan-3-carboxylic acid methyl ester (0.160 g, 0.3 mmol) and lithium hydroxide (0.082 g,. 3.4 mmol) in THF:methanol:water (3: 2:2 mL) was stirred at 25° C. for 19 h. The solution was then washed 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-furan-3-carboxylic acid as a crude solid (0.160 g, 100%). MS: 457 (M+H)+

Workup

  1. washThe solution was then washed with ethyl acetate (2×30 mL)
  2. washThe aqueous layer was washed with ethyl acetate (3×40 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3431c743345a49c288589f4c8b5cc26d
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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