Methanol → 4-[4-(4-Pyridin-3-yl-phenyl)piperazine-1-sulfonylmethyl]tetrahydropyran-4-carboxylic acid

HRID 1005847Notes

Reaction equation

HRID 1005847 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][S:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].O.[OH-].[Li+].CO.O>O1CCCC1>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:24]2[CH:23]=[CH:22][C:21]([N:18]3[CH2:19][CH2:20][N:15]([S:12]([CH2:11][C:5]4([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]4)(=[O:14])=[O:13])[CH2:16][CH2:17]3)=[CH:26][CH:25]=2)[CH:28]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 698951164-[4-(4-Pyridin-3-yl-phenyl)piperazine-1-sulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl ester

Product 1

HCID 226467164-[4-(4-Pyridin-3-yl-phenyl)piperazine-1-sulfonylmethyl]tetrahydropyran-4-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[4-(4-Pyridin-3-yl-phenyl)piperazine-1-sulfonylmethyl]tetrahydropyran-4-carboxylic acid methyl ester (0.19 g) and lithium hydroxide monohydrate (0.087 g) were combined in tetrahydrofuran (10 ml), methanol (5 ml) and water (5 ml) and heated to reflux for 2 h. The solvents were then removed in vacuo and the residue diluted with 1 M sodium hydroxide (50 ml) and washed with ethyl acetate (3×20 ml). The aqueous phase was then acidified pH 5 and the suspension formed extracted with 10% methanol/dichloromethane (5×40 ml). The combined extracts were then washed with water (2×20 ml), saturated brine (20 ml), dried (Na2SO4) and reduced in vacuo to provide the title compound as a white solid (0.13 g, 72%).

Workup

  1. temperatureto reflux for 2 h
  2. customThe solvents were then removed in vacuo
  3. additionthe residue diluted with 1 M sodium hydroxide (50 ml)
  4. washwashed with ethyl acetate (3×20 ml)
  5. customthe suspension formed
  6. extractionextracted with 10% methanol/dichloromethane (5×40 ml)
  7. washThe combined extracts were then washed with water (2×20 ml), saturated brine (20 ml)
  8. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-99c68f13ba6a44f2bbec075989eca431
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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