Calcium Carbonate → HCID 22810249, compound

HRID 1701235Notes

Reaction equation

HRID 1701235 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([OH:25])[CH2:12][C@@H:11]1[OH:26].C(=O)([O-])[O-].[Ca+2].[OH-].[Na+].[BH4-].[Na+]>C([O-])(=O)C.[Hg+2].C([O-])(=O)C.O1CCCC1>[OH:25][C@@H:13]1[CH2:12][C@H:11]2[C@H:10]([CH2:9][C@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:27])[O:26]2)[C@H:14]1/[CH:15]=[CH:16]/[C@@H:17]([OH:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 10112Calcium CarbonateHCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 13053926HCID 13053926, compound

Product 1

HCID 22810249HCID 22810249, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 480 mg. of (5Z,13E)-(9S,11R,15S)-9,11,15-trihydroxy-19-methyl-5,13,18-prostatrienoic acid methyl ester (prepared according to DOS No. 2,635,985) and 530 mg. of mercury(II) acetate in 20 ml. of tetrahydrofuran is stirred with 200 mg. of pulverized calcium carbonate for 48 hours at 25°, and then combined in succession at 0° with 8 ml. of 1 N sodium hydroxide solution and a solution of 200 mg. of sodium borohydride in 8 ml. of 1 N sodium hydroxide solution. The mixture is stirred for 10 minutes and poured on 100 ml. of citrate buffer (pH 4), whereafter it is extracted three times with respectively 50 ml. of methylene chloride. The extract is shaken with sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated under vacuum. The residue shows, in the thin-layer chromatogram in the system ether/dioxane (9+1), two spots which are more nonpolar as compared to the starting material. For purposes of purification, the product is chromatographed on silica gel with the use of a hexane/ethyl acetate gradient, thus obtaining 100 mg. of the nonpolar isomer and 210 mg. of the polar isomer, both in the form of oils.

Workup

  1. customcombined in succession at 0° with 8 ml
  2. additionpoured on 100 ml
  3. extractionof citrate buffer (pH 4), whereafter it is extracted three times with respectively 50 ml
  4. stirringThe extract is shaken with sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customFor purposes of purification
  8. customthe product is chromatographed on silica gel with the use of a hexane/ethyl acetate gradient
  9. customthus obtaining 100 mg

Sources & evidence

ORD record
ord-7466a2e1effc426aa46233312f396bf9
Source dataset
uspto-grants-1980_03
Patent number
US04191694

Reaction notes

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