Iodine → HCID 86737311, compound

HRID 224326Notes

Reaction equation

HRID 224326 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:34])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][C@@H:16]1[C@@H:20](/[CH:21]=[CH:22]/[C@@H:23]([OH:31])[CH:24]([CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28][Cl:29])[C@H:19]([OH:32])[CH2:18][C@@H:17]1[OH:33].[I:35]I>C(Cl)Cl.C(OCC)C>[CH3:7][O:8][C:9](=[O:34])[CH2:10][CH2:11][CH2:12][CH:13]([I:35])[CH:14]1[O:33][C@H:17]2[CH2:18][C@@H:19]([OH:32])[C@H:20](/[CH:21]=[CH:22]/[C@@H:23]([OH:31])[CH:24]([CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28][Cl:29])[C@H:16]2[CH2:15]1

Participants

6

Reactant 3

HCID 807IodineHCID 11430Potassium CarbonateHCID 70595439HCID 70595439, compound

Product 1

HCID 86737311HCID 86737311, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of nitrogen, 194 mg of anhydrous potassium carbonate was added to a solution of 140 mg of (5Z,13E)-(9α,11α,15S,16RS)-9,11,15-trihydroxy-16-methyl-20-chloroprosta-5,13-dienoic acid methyl ester [prepared as described in Example 8 of British Patent Application No. 22090/75 and e.g. the equivalent Belgian Specification No. 842,113] in 5 ml of methylene chloride. To the reaction mixture was added 200 mg of iodine in portions during 2 hours with stirring at 0° C. The reaction mixture was diluted with diethyl ether, washed with an aqueous solution of sodium thiosulphate, water and an aqueous solution of sodium chloride, dried over anhydrous 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 (2:1) as eluent to give 135 mg of the title compound having the following physical characteristics:

Workup

  1. customprepared
  2. washwashed with an aqueous solution of sodium thiosulphate, water
  3. dry with materialan aqueous solution of sodium chloride, dried over anhydrous magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-89f39228e5dc4b688f86a3a330e18389
Source dataset
uspto-grants-1980_11
Patent number
US04232009

Reaction notes

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