반응 #76099

반응 방정식

2-propane thiol

HCl

potassium tert-butoxide

tetrahydrofuran

methanesulfonyl chloride

3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester

→

3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-isopropylsulfanyl-propionic acid ethyl ester

용매

CH2Cl2

pyridine

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred overnight
2. 2
   추출The mixture was extracted with diethyl ether (3×)
3. 3
   세척washed with 1 M HCl (2×), saturated brine (2×)
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated to a crude film
6. 6
   기타The film was purified by chromatography on silica gel (Merck silica gel 60, art#9385-3)
7. 7
   세척eluting with 20% ethyl acetate in hexanes

실험 절차

To a solution of 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester (0.69 mmol, 300 mg) dissolved in pyridine (3 mL) was added methanesulfonyl chloride (0.69 mmol, 0.534 mL). The mixture was stirred at room temperature overnight. A portion of the reaction mixture (0.115 mmol) was added to a solution containing 2-propane thiol (0.115 mmol, 0.107 mL) dissolved in anhydrous CH2Cl2 (2 mL). To this stirred solution was added a 1M solution of potassium tert-butoxide in tetrahydrofuran (0.115 mmol, 0.115 mL). The mixture was stirred overnight then poured over 1 M HCl. The mixture was extracted with diethyl ether (3×). The organic layers were combined, washed with 1 M HCl (2×), saturated brine (2×), dried over Na2SO4, and concentrated to a crude film. The film was purified by chromatography on silica gel (Merck silica gel 60, art#9385-3) eluting with 20% ethyl acetate in hexanes to give 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-isopropylsulfanyl-propionic acid ethyl ester as a clear film containing an approximate 1:1 mixture of methyl and ethyl ester (30.2 mg, 55%).

출처