تفاعل #1793604

معادلة التفاعل

(13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid 2-propoxyethyl ester

DBU

hydrochloric acid

phosphate

→

title compound

المردود 68.5%

(5Z,13E)-(9α,11α,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoic acid 2-propoxyethyl ester

المردود 68.5%

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solution obtained
2. 2
   درجة الحرارةwas cooled to 0°-5° C.
3. 3
   workup.ADDITIONwere added
4. 4
   استخلاصthe mixture was extracted with diethyl ether
5. 5
   تجفيفThe extract was dried over magnesium sulphate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by column chromatography on Florisil using as eluent
8. 8
   workup.ADDITIONa mixture of ethyl acetate and n-hexane (1:4)
9. 9
   workup.ADDITIONcontaining 0.1% v/v of triethylamine

الإجراء التجريبي

235 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid 2-propoxyethyl ester (prepared as described in Example 5) and 0.8 ml of DBU were stirred at 50°-60° C. for 3 hours under a nitrogen atmosphere. The solution obtained was cooled to 0°-5° C., 4 ml of 1 N hydrochloric acid and 4 ml of a phosphate buffer with a pH of 6.86, cooled to 0°-5° C., were added and the mixture was extracted with diethyl ether. The extract was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on Florisil using as eluent a mixture of ethyl acetate and n-hexane (1:4) containing 0.1% v/v of triethylamine to give 136 mg of the title compound having the following physical characteristics.

المصدر