Carbon Dioxide → HCID 70416995, compound

HRID 1105646Notes

Reaction equation

HRID 1105646 reaction equation
[Br-].[C:2]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:42])[CH2:19][CH2:20][CH2:21][CH2:22][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:13][CH:12]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:43][S:44]([CH3:46])=O.[H-].[Na+].[C:49](=[O:51])=O.[OH2:52]>C(OCC)(=O)C>[C:2]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18](=[O:42])[CH2:19][CH2:20][CH2:21][CH:22]=[CH:16][CH2:11][C@@H:12]2[C@@H:43]([S:44][CH2:46][C:3]([OH:52])([CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:14]([OH:17])[CH2:13][CH:49]2[OH:51])=[CH:15][CH:16]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 679Dimethyl Sulfoxide3×HCID 962WaterHCID 24758Sodium hydrideHCID 86738202HCID 86738202, compound

Product 1

HCID 70416995HCID 70416995, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen a solution of 5.6 g. of 5-triphenylphosphoniopentanoic acid p-benzoylaminophenyl ester bromide, dissolved in 15 ml. of dry DMSO was dropped into a stirred solution which had been obtained by the addition of 0.75 g. of NaH (as a 50% suspension in mineral oil) to 10 ml. of dry DMSO. The mixture was maintained for 1 hour at 80° C. After cooling to room temperature, there was added dropwise, under nitrogen and with stirring, 3 g. of 2-oxa-3,7-dihydroxy-6-(2-hydroxy-2-methyl-heptylmercapto)-bicyclo[3.3.0]octane, dissolved in 5 ml. of dry DMSO, to the solution of the phosphorylide. The solution was stirred for a further 2 hours at 50° C. After cooling, the reaction mixture was poured into a mixture consisting of 10 ml. of ethyl acetate, 40 g of dry ice and 50 ml of water. The organic phase was separated off. The aqueous phase was washed three times with 50 ml amounts of ethyl acetate containing 20 g. of dry ice. The combined organic phases were washed with water and dried over MgSO4. The solvent was distilled off. After chromatographic purification of the residue (silica gel/chloroform), 9,11,15-trihydroxy-15-methyl-13-thia-5-prostenoic acid p-benzoylaminophenyl ester was obtained.

Workup

  1. customhad been obtained by the addition of 0.75 g
  2. temperatureAfter cooling to room temperature
  3. additionthere was added dropwise, under nitrogen
  4. stirringThe solution was stirred for a further 2 hours at 50° C
  5. temperatureAfter cooling
  6. additionthe reaction mixture was poured into a mixture
  7. customThe organic phase was separated off
  8. washThe aqueous phase was washed three times with 50 ml amounts of ethyl acetate containing 20 g
  9. washThe combined organic phases were washed with water
  10. dry with materialdried over MgSO4
  11. distillationThe solvent was distilled off
  12. customAfter chromatographic purification of the residue (silica gel/chloroform)

Sources & evidence

ORD record
ord-802e15147ad543349705ebac55edc64f
Source dataset
uspto-grants-1982_01
Patent number
US04309441

Reaction notes

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