반응 #304178

반응 방정식

3-mercapto-2-hydroxypropyl-cholesterol

acetic acid

→

cholesterol

용매

DMAc

DMAc

DMAc

반응 조건

후처리

1. 1
   workup.ADDITIONThe bromobutylated Tecothane (1.14 g, containing approximately 0.5 mmol of 4-bromobutyl groups)
2. 2
   여과The reaction solution was then filtered
3. 3
   기타the polymer was precipitated with methanol (150 ml)
4. 4
   세척The precipitate was washed with methanol alternating with 2-propanol
5. 5
   workup.STIRRINGstirred consequently with large amounts of 2-propanol, methanol, and water
6. 6
   기타dried under 0.05 mm Hg conditions

실험 절차

The bromobutylated Tecothane (1.14 g, containing approximately 0.5 mmol of 4-bromobutyl groups) described above was dissolved in DMAc (20 ml) under argon and cooled to −2° C. A solution of 3-mercapto-2-hydroxypropyl-cholesterol (0.495 g, 1.04 mmol) in DMAc (8 ml) was added and a freshly prepared 0.12 M DMAc-solution of (Bu4N)2B4O7 (5 ml, 6 mmol) was also added. The mixture was stirred at −1 to 1° C. for one hour and acidified with acetic acid (0.12 ml, 2 mmol). The reaction solution was then filtered and the polymer was precipitated with methanol (150 ml). The precipitate was washed with methanol alternating with 2-propanol and stirred consequently with large amounts of 2-propanol, methanol, and water and dried under 0.05 mm Hg conditions. The procedure yielded 1.31 g of cholesterol-modified Tecothane. 1H NMR analysis of this polymer (DMF-d7) indicated covalent attachment of cholesterol to 20% of the urethane segments via noncleavable sulfide bonds (see FIG. 2) corresponding to approximately 0.4 mmol of pendant cholesterol moieties per gram of polymer.

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