تفاعل #554575

ord-0c3f2de7ecae4ff483c3d51b7ba30cc8

معادلة التفاعل

COC(=O)CCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
15a
COC(=O)CCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
Methyl 6-trityloxy-hexanoate
COC(=O)CCCCCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
15b
COC(=O)CCCCCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
Methyl-9-trityloxy-nonanoate
COC(=O)CCCCCCCCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
15c
COC(=O)CCCCCCCCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
Methyl-12-trityloxy-dodecanoate
O=C(O)CCCCCCCCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
12-trityloxydodecanoic acid
O=C(O)CCCCCCCCCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
12-Trityloxy-dodecanoic acid

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةduring which the pH was maintained above 4
  2. 2
    أخرىAfter recrystallization for solid product or flash chromatography for oil products, 6-trityloxyhexanoic acid 16a, 9-trityloxynonanoic acid 16b

الإجراء التجريبي

Hydrolysis of the methyl ester of 15a, 15b, and 15c was carried out under basic conditions, followed by an acidic work up, during which the pH was maintained above 4 to prevent trityl deprotection. After recrystallization for solid product or flash chromatography for oil products, 6-trityloxyhexanoic acid 16a, 9-trityloxynonanoic acid 16b and 12-trityloxydodecanoic acid 16c were isolated, providing aliphatic side-chains that were ready to be coupled to 12 and 13.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08623326B2uspto-grants-2014_01