Reaktion #2012735

Reaktionsgleichung

lithium hydroxide monohydrate

3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid methyl ester

compound 129

3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid methyl ester

MeOH THF

→

3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid

Ausbeute 55.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenConcentration in vacuo
2. 2
   Waschenwashed with EA
3. 3
   Sonstigewas then adjusted to pH ˜2 with 2M hydrochloric acid at 0° C
4. 4
   FiltrationThe resulting precipitate was filtered off
5. 5
   Einengenconcentrated in vacuo
6. 6
   WaschenThe residue was washed with an ether/pentane mixture (1:4 vv)

Vorschrift

A solution of 120 mg (2.92 mmol) of lithium hydroxide monohydrate in water (4 ml) was added to a solution of 320 mg (0.73 mmol) of 3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid methyl ester (exemplary compound 129) in a MeOH/THF mixture (2:1 vv, 9 ml), and the mixture was stirred for 16 h at RT. Concentration in vacuo was then carried out. The residue was taken up in water and washed with EA. The aqueous phase was then adjusted to pH ˜2 with 2M hydrochloric acid at 0° C. The resulting precipitate was filtered off, taken up in toluene and concentrated in vacuo. The residue was washed with an ether/pentane mixture (1:4 vv), yielding 170 mg (0.4 mmol, 55%) of 3-[[[2-[3-(4-fluorophenyl)-propylsulfanyl]-pyridine-3-carbonyl]amino]-methyl]-benzoic acid. MS: m/z 425.1 [m+H]+.

Quelle