Hydrochloric Acid → HCID 86737038, compound

HRID 1706423Notes

Reaction equation

HRID 1706423 reaction equation
[CH2:1]([O:3][C:4]([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)=[O:5])[CH3:2].C1CCN2C(=NCCC2)CC1.Cl.P([O-])([O-])([O-])=O>>[CH2:1]([O:3][C:4]([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)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86737039HCID 86737039, compound

Product 1

HCID 86737038HCID 86737038, compoundYield 74.7%

Procedure

A mixture of 287 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid ethoxycarbonylmethyl ester (prepared as described in Example 7) and 1 ml of DBU was stirred for 2.5 hours at 50°-60° C. under a nitrogen atmosphere. The solution obtained was cooled to 0° C.-5° C., 5 ml of 1 N hydrochloric acid and 5 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 (1:1) containing 0.1% v/v of triethylamine to give 181 mg of the title compound having the following physical characteristics.

Workup

  1. customThe solution obtained
  2. temperaturewas cooled to 0° C.-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 (1:1)
  9. additioncontaining 0.1% v/v of triethylamine

Sources & evidence

ORD record
ord-8b35765e842548f6837f8b7f8f173ebc
Source dataset
uspto-grants-1980_06
Patent number
US04207332

Reaction notes

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