Chloroform → HCID 86737312, compound

HRID 224328Notes

Reaction equation

HRID 224328 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:35])[CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][C@@H:18]1[C@@H:22](/[CH:23]=[CH:24]/[C@@H:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])[C@H:21]([OH:33])[CH2:20][C@@H:19]1[OH:34].C(Cl)(Cl)Cl.O1CCCC1>C(OCC)(=O)C>[CH3:9][O:10][C:11](=[O:35])[CH2:12][CH2:13][CH2:14][CH:15]([Br:1])[CH:16]1[O:34][C@H:19]2[CH2:20][C@@H:21]([OH:33])[C@H:22](/[CH:23]=[CH:24]/[C@@H:25]([OH:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])[C@H:18]2[CH2:17]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 70596939HCID 70596939, compound

Product 1

HCID 86737312HCID 86737312, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of nitrogen, 85 mg of N-bromosuccinimide were added to a solution of 175 mg of (5Z,13E)-(9α,11α,15S)-9,11,15-trihydroxy-20-chloroprosta-5,13-dienoic acid methyl ester [prepared as described in Example 4 of British Patent Application No. 22090/75 and, e.g. the equivalent Belgian Specification No. 842113] in 3 ml of a mixture of chloroform and tetrahydrofuran (1:1) and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was diluted with ethyl acetate and washed with an aqueous solution of sodium chloride, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:2) as eluent to give 165 mg of the title compound having the following physical characteristics:

Workup

  1. customprepared
  2. washwashed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium 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 (1:2) as eluent

Sources & evidence

ORD record
ord-e343abd145a345468b6a3a5b5909462d
Source dataset
uspto-grants-1980_11
Patent number
US04232009

Reaction notes

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