HCID 11823843, compound → HCID 22874409, compound

HRID 263441Notes

Reaction equation

HRID 263441 reaction equation
Cl.O1CCOCC1.[CH2:8]([O:15][C:16]([C@H:18]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([O:15][C:16]([C@H:18]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][C:20]([OH:22])=[O:21])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11823843HCID 11823843, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 22874409HCID 22874409, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 4M hydrochloric acid-dioxane solution (15 ml) was added to tert-butyl 3-(R)-benzyloxycarbonyloctanoate (983 mg), prepared in Referential Example 6, and the resulting mixture was stirred overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel, using a 30:1 mixture of chloroform and methanol as an eluent, to give 838 mg of the desired compound as a colorless oil.

Workup

  1. customprepared in Referential Example 6
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. additiona 30:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-e468d6c4383744c1a6ef099f84946c29
Source dataset
uspto-grants-1997_07
Patent number
US05643908

Reaction notes

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