Reaktion #2133132

Reaktionsgleichung

(Methylthio)acetic acid

PyBOP

Hünig base

C-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-methylamine

→

N-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-ylmethyl}-2-methylsulfanyl-acetamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction is quenched with water
2. 2
   ExtraktionThe reaction mixture is extracted three times with dichloromethane
3. 3
   ExtraktionThe combined organic phases are extracted with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude product is purified on a semi-preparative HPLC

Vorschrift

(Methylthio)acetic acid (29 μl), PyBOP (126 mg) and Hünig base (115 μl) is added to a solution of C-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-methylamine (90 mg) in dichloromethane (2 ml). After 1 hour at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with dichloromethane. The combined organic phases are extracted with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield N-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-ylmethyl}-2-methylsulfanyl-acetamide (82 mg, compound 1.10 in Table 1) as a white foam. MS (HPLC/MS): 497 (MH+). Retention time: 2.00 min.

Quelle