Lithium hydroxide, monohydrate → 3-Methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzoic acid

HRID 1373107Notes

Reaction equation

HRID 1373107 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:14]=1)[C:8]([O:10]C)=[O:9])(=[O:4])=[O:3].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:14]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21074201Methyl 3-methylsulfonyl-5-(2-oxopyrrolidin-1-yl)-benzoate

Product 1

HCID 210741993-Methylsulfonyl-5-(2-oxopyrrolidin-1-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-methylsulfonyl-5-(2-oxopyrrolidin-1-yl)-benzoate (D18) (0.717 g) was suspended in dioxan (3.6 ml) and treated with a solution of lithium hydroxide monohydrate (0.153 g) in water (3.6 ml). The mixture was stirred for 2 h at room temperature and a clear solution was formed. The pH was adjusted to ˜4 by addition of Amberlyst-15 H+ resin. The resin was removed by filtration and washed well with dioxan. The combined filtrates were evaporated and the residue dried. Trituration with ether gave D19 (0.51 g) as a pale cream solid.

Workup

  1. customa clear solution was formed
  2. additionThe pH was adjusted to ˜4 by addition of Amberlyst-15 H+ resin
  3. customThe resin was removed by filtration
  4. washwashed well with dioxan
  5. customThe combined filtrates were evaporated
  6. customthe residue dried
  7. customTrituration with ether gave D19 (0.51 g) as a pale cream solid

Sources & evidence

ORD record
ord-d95b5c951a5d4800a85ef027b5d38b9a
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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