Sodium Hydroxide → (R)-(+)-3-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl)oxy]benzoic acid

HRID 75979Notes

Reaction equation

HRID 75979 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:33]=[CH:32][C:12]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@@H:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])[CH:23]=3)[C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=2)=[N:6][N:5]=1>CO.O>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:33]=[CH:32][C:12]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@@H:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])[CH:23]=3)[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)=[N:6][N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86668095(R)-(+)-Methyl 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl) oxy]benzoate2×

Product 1

HCID 68107027(R)-(+)-3-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl)oxy]benzoic acidYield 71.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium hydroxide (pallets, 0.35 g) was added To a stirring mixture of (R)-(+)-Methyl 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl) oxy]benzoate (1.1 g) (Intermediate 19) in MeOH:H2O (1:1) at room temperature. The reaction was monitored by TLC. After completion, methanol was evaporated from the reaction mixture and water was added. The aqueous layer was washed with EtOAc, acidified with dil. HCl (0.05 N) to obtain solid. The solid obtained was filtered, washed with water, dried under suction or vacuum to get pure white solid (0.76 g).

Workup

  1. customAfter completion, methanol was evaporated from the reaction mixture and water
  2. additionwas added
  3. washThe aqueous layer was washed with EtOAc
  4. customto obtain solid
  5. customThe solid obtained
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried under suction or vacuum

Sources & evidence

ORD record
ord-1a0c9d25475c4df3b7e74b4dccc649c0
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

Loading…