Lithium Hydroxide → HCID 67044091, compound

HRID 1944452Notes

Reaction equation

HRID 1944452 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[C:21]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:20][N:19]=[C:18]([S:31][CH3:32])[N:17]=2)=[C:6]1[CH3:33].[OH-].[Li+]>O1CCCC1>[C:25]1([S:22]([C:21]2[C:16]([CH2:15][C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[N:5]([CH2:4][C:3]([OH:34])=[O:2])[C:6]=3[CH3:33])=[N:17][C:18]([S:31][CH3:32])=[N:19][CH:20]=2)(=[O:23])=[O:24])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67043735HCID 67043735, compound

Product 1

HCID 67044091HCID 67044091, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(5-benzenesulfonyl-2-methylsulfanylpyrimidin-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.23 g) and tetrahydrofuran (30 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.93 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, the pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume) to afford the title compound as a yellow solid (0.20 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative reverse-phase HPLC
  9. washeluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume)

Sources & evidence

ORD record
ord-7fa3ac40683545a2969a465a8aac00af
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

Loading…