Hydrochloric Acid → HCID 86737034, compound

HRID 1706421Notes

Reaction equation

HRID 1706421 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](=[O:32])[CH2:9][CH2:10][CH2:11][CH:12](Br)[CH:13]1[O:30][C@H:16]2[CH2:17][C@@H:18]([OH:29])[C@H:19](/[CH:20]=[CH:21]/[C@@H:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@H:15]2[CH2:14]1.C1CCN2C(=NCCC2)CC1.Cl.P([O-])([O-])([O-])=O>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](=[O:32])[CH2:9][CH2:10][CH2:11]/[CH:12]=[C:13]1/[CH2:14][C@@H:15]2[C@@H:19](/[CH:20]=[CH:21]/[C@@H:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@H:18]([OH:29])[CH2:17][C@@H:16]2[O:30]/1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86737035HCID 86737035, compound

Product 1

HCID 86737034HCID 86737034, compoundYield 64.9%

Procedure

197 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid 5-hydroxypentyl ester (prepared as described in Example 3) and 0.66 ml of DBU were stirred for 3 hours at 50°-60° C. under a nitrogen atmosphere. The solution obtained was cooled to 0°-5° C., 3.3 ml of 1 N hydrochloric acid and 3.3 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" (an activated magnesium silicate: "Florisil" is a registered Trade Mark of Florin Co.) using as eluent ethyl acetate containing 0.1% v/v of triethylamine to give 108 mg of the title compound having the following physical characteristics.

Workup

  1. customThe solution obtained
  2. temperaturewas cooled to 0°-5° C.
  3. additionwere added
  4. extractionthe mixture was extracted with diethyl ether
  5. dry with materialThe extract was dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on "Florisil" (an activated magnesium silicate

Sources & evidence

ORD record
ord-7324071629d046edab10bbe0a6aebf16
Source dataset
uspto-grants-1980_06
Patent number
US04207332

Reaction notes

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