Hydrochloric Acid → HCID 86737309, compound

HRID 224327Notes

Reaction equation

HRID 224327 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6][CH:7](I)[CH:8]1[O:27][C@H:11]2[CH2:12][C@@H:13]([OH:26])[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:25])[CH:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23])[C@H:10]2[CH2:9]1.Cl.P([O-])([O-])([O-])=O>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8]1/[CH2:9][C@@H:10]2[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:25])[CH:18]([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23])[C@H:13]([OH:26])[CH2:12][C@@H:11]2[O:27]/1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 86737311HCID 86737311, compound

Product 1

HCID 86737309HCID 86737309, compoundYield 58.6%

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of nitrogen, a solution of 116 mg of (13E)-(5RS,6RS,9α,11α,15S,16RS)-5-iodo-6,9-epoxy-11,15-dihydroxy-16-methyl-20-chloroprost-13-enoic acid methyl ester (prepared as described in Example 1) and 0.4 ml of 1,5-diazabicyclo[5,4,0]undecene-5 (DBU) was stirred at room temperature for 18 hours, and then cooled to 0° C. To the reaction mixture were added 2 ml of 1 N hydrochloric acid and 2 ml of phosphate buffer solution (pH 6.86) with cooling to 0° C. The reaction mixture was extracted quickly with diethyl ether. The extract was dried over anhydrous 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 a mixture of ethyl acetate and n-hexane (1:1) containing 0.1% of triethylamine as eluent to give 52 mg 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 anhydrous magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on Florisil (an activated magnesium silicate
  6. additiona mixture of ethyl acetate and n-hexane (1:1)
  7. additioncontaining 0.1% of triethylamine as eluent

Sources & evidence

ORD record
ord-043db795314749b5b2413e2169dd12e6
Source dataset
uspto-grants-1980_11
Patent number
US04232009

Reaction notes

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