Hydrochloric Acid → HCID 86737032, compound

HRID 1706420Notes

Reaction equation

HRID 1706420 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9](=[O:33])[CH2:10][CH2:11][CH2:12][CH:13](Br)[CH:14]1[O:31][C@H:17]2[CH2:18][C@@H:19]([OH:30])[C@H:20](/[CH:21]=[CH:22]/[C@@H:23]([OH:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@H:16]2[CH2:15]1)[CH2:4][CH3:5])[CH3:2].Cl.P([O-])([O-])([O-])=O>>[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9](=[O:33])[CH2:10][CH2:11][CH2:12]/[CH:13]=[C:14]1/[CH2:15][C@@H:16]2[C@@H:20](/[CH:21]=[CH:22]/[C@@H:23]([OH:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@H:19]([OH:30])[CH2:18][C@@H:17]2[O:31]/1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 86737033HCID 86737033, compound

Product 1

HCID 86737032HCID 86737032, compoundYield 28.8%

Procedure

123 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid 2-(N,N-diethylamino)ethyl ester (prepared as described in Example 1) and 0.4 ml of DBU (1,5-diazabicyclo[5.4.0]-undecene-5) were stirred at 50°-60° C. for 3 hours under a nitrogen atmosphere. The solution obtained was cooled to 0°-5° C., 2.5 ml of 1 N hydrochloric acid and 2 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 washed with water 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 as eluent a mixture of diethyl ether and acetone (6:1) containing 0.1% v/v of triethylamine to give 30 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. washThe extract was washed with water
  6. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using as eluent
  9. additiona mixture of diethyl ether and acetone (6:1)
  10. additioncontaining 0.1% v/v of triethylamine

Sources & evidence

ORD record
ord-438d4d76c3e4408a8566338d83bd5f06
Source dataset
uspto-grants-1980_06
Patent number
US04207332

Reaction notes

Loading…