Hydrochloric Acid → HCID 86737036, compound

HRID 1706422Notes

Reaction equation

HRID 1706422 reaction equation
[CH2:1]([O: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)[CH2:2][CH3:3].C1CCN2C(=NCCC2)CC1.Cl.P([O-])([O-])([O-])=O>>[CH2:1]([O: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)[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86737037HCID 86737037, compound

Product 1

HCID 86737036HCID 86737036, compoundYield 68.5%

Procedure

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.

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 using as eluent
  8. additiona mixture of ethyl acetate and n-hexane (1:4)
  9. additioncontaining 0.1% v/v of triethylamine

Sources & evidence

ORD record
ord-d43a2a3f0a8a4c979aaf0c21cf775a1d
Source dataset
uspto-grants-1980_06
Patent number
US04207332

Reaction notes

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