Lithium Hydroxide → HCID 117600029, compound

HRID 1746462Notes

Reaction equation

HRID 1746462 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][CH:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Br:20])[CH:14]=1)[C:7]1[S:8][C:9]([CH3:12])=[CH:10][N:11]=1)C.[Li+].[OH-]>C1COCC1.CO.O>[Br:20][C:15]1[CH:14]=[C:13]([CH:6]([C:7]2[S:8][C:9]([CH3:12])=[CH:10][N:11]=2)[CH2:5][C:4]([OH:21])=[O:3])[CH:18]=[C:17]([Cl:19])[CH:16]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117600281HCID 117600281, compound

Product 1

HCID 117600029HCID 117600029, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

17 g (43.73 mmol) of 3-(3-Bromo-5-chloro-phenyl)-3-(5-methyl-thiazol-2-yl)-propionic acid ethyl ester are dissolved in 30 ml of a THF/MeOH/H2O=2:1:1 mixture and LiOH (2Eq) is added. After stirring overnight at RT, the solvent is removed in vacuo and the crude material is treated with 30 ml of EtOAc and 30 ml of water with pH=4. The organic phase is separated, dried over Na2SO4 and the solvent removed in vacuo. The crude material is recrystallized from heptane/EtOAc mixtures delivering 9.2 g (Yield=58%) of 3-(3-Bromo-5-chloro-phenyl)-3-(5-methyl-thiazol-2-yl)-propionic acid.

Workup

  1. additionis added
  2. customthe solvent is removed in vacuo
  3. additionthe crude material is treated with 30 ml of EtOAc and 30 ml of water with pH=4
  4. customThe organic phase is separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed in vacuo
  7. customThe crude material is recrystallized from heptane/EtOAc

Sources & evidence

ORD record
ord-8423b48c22b74c208429180bdc9fa2b4
Source dataset
uspto-grants-2015_10
Patent number
US09150526B2

Reaction notes

Loading…