Hydrochloric Acid → HCID 70575767, compound

HRID 1277698Notes

Reaction equation

HRID 1277698 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][CH2:6][CH:7](Br)[CH:8]1[O:38][C@H:11]2[CH2:12][C@@H:13]([O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)[C@@H:18]([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1.C1CCN2C(=NCCC2)CC1.Cl.P([O-])([O-])([O-])=[O:54]>O1CCCC1.C(O)(=O)C.O>[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[C@@H:18]([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:12][C@@H:11]1[OH:54]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86737126HCID 86737126, compound

Product 1

HCID 70575767HCID 70575767, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of nitrogen, a solution of 2.233 g of (13E)-(5RS,6RS,9α,11α,15S,16S)-5-bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)-16-methylprost-13-enoic acid methyl ester [prepared as described in Reference Example 1(a)] and 7.4 ml of DBU was stirred at 70° C. for 3 hours, and then cooled to 0° C. To the reaction mixture were added 37 ml of 1 N hydrochloric acid and 37 ml of phosphate buffer solution (pH 6.68) with cooling to 0° C. The reaction mixture was extracted quickly with diethyl ether. The extract was dried over magnesium sulphate and concentrated under reduced pressure to give an oily product. To a solution of the oily product thus obtained in 40 ml of tetrahydrofuran were added dropwise 4 ml of water and 4 ml of 65% (v/v) aqueous acetic acid and the mixture was stirred at room temperature for 2 hours and then extracted with ethyl acetate. The extract was washed with water, an aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 1.323 g of the title compound having the following physical characteristics:

Workup

  1. temperaturewith cooling to 0° C
  2. extractionThe reaction mixture was extracted quickly with diethyl ether
  3. dry with materialThe extract was dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto give an oily product
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialan aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, dried over magnesium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel using
  11. additiona mixture of cyclohexane and ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-7fc1cee681a240c297f22f773c6fef59
Source dataset
uspto-grants-1981_07
Patent number
US04278688

Reaction notes

Loading…