HCID 86747815, compound → HCID 86747816, compound

HRID 1033098Notes

Reaction equation

HRID 1033098 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17]CC4C=CC=CC=4)=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:25](=[S:28])[CH2:26][CH3:27])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)=O.Cl.CCOCC>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[C:9]([C:25](=[S:28])[CH2:26][CH3:27])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 86747815HCID 86747815, compound

Product 1

HCID 86747816HCID 86747816, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of methylthioacetyl derivative from Step 4 (140 mg) in AcOH (1 mL) and conc. HCl (1 mL) was stirred at r.t. 18 hr. The reaction mixture was diluted with Et2O, washed with H2O (2×), saturated NaHCO3 solution, brine, dried over MgSO4 and the solvent evaporated. The residue was flash chromatographed, eluting with hexane:EtOAc:CH2Cl2 (85:15:50) to afford the title compound as a foam.

Workup

  1. custom18 hr
  2. washwashed with H2O (2×), saturated NaHCO3 solution, brine
  3. dry with materialdried over MgSO4
  4. customthe solvent evaporated
  5. customchromatographed
  6. washeluting with hexane:EtOAc:CH2Cl2 (85:15:50)

Sources & evidence

ORD record
ord-e5a0951affff4f1caec3eaf310cdbbaf
Source dataset
uspto-grants-1994_05
Patent number
US05308852

Reaction notes

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