Reaktion #53943

ord-eb149397390941fca0930530fc7bff5a

Reaktionsgleichung

O=S(=O)([O-])O.[K+]
KHSO4
COC(=O)CCO[C@H]1CC[C@H](N(C)S(=O)(=O)c2ccc(C(F)(F)F)cc2)CC1
trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester
[Li+].[OH-]
LiOH
→
CN([C@H]1CC[C@H](OCCC(=O)O)CC1)S(=O)(=O)c1ccc(C(F)(F)F)cc1
trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid
Ausbeute 99.5%

Edukte

O=S(=O)([O-])O.[K+]
KHSO4
COC(=O)CCO[C@H]1CC[C@H](N(C)S(=O)(=O)c2ccc(C(F)(F)F)cc2)CC1
trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester
[Li+].[OH-]
LiOH

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe mixture was extracted with EtOAc
  2. 2
    WaschenThe organic phase was washed with brine
  3. 3
    Trocknendried over Na2SO4
  4. 4
    Sonstigeevaporated

Vorschrift

1.14 g (2.7 mmol) trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester in 27 ml THF were treated with 27 ml 1M LiOH for 1 h at RT. The was acidified by adding 1M KHSO4, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated to give 1.1 g (quant.) trans-3-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid as colorless oil, MS: 408 (M−H)−.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02