HCID 15518070, compound → HCID 10222392, compound

HRID 278539Notes

Reaction equation

HRID 278539 reaction equation
O1CCCCC1[O:7][C@@H:8]1[CH2:12][C@H:11]([O:13]C2CCCCO2)[C@H:10]([CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][C:25](=[O:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@H:9]1/[CH:32]=[CH:33]/[C@@H:34]([O:40]C1CCCCO1)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>CO>[OH:7][C@@H:8]1[CH2:12][C@H:11]([OH:13])[C@H:10]([CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][C:25](=[O:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@H:9]1/[CH:32]=[CH:33]/[C@@H:34]([OH:40])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

3

Reactant 1

HCID 15518070HCID 15518070, compound

Product 1

HCID 10222392HCID 10222392, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the acetate of Example 25 (36 mg, 0.055 mmol) and PPTs (2 mg) in MeOH (1.0 mL) was stirred at 45° C. for 4 h. The reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was diluted with EtOAc and washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 50%-100% EtOAc/hex) afforded 18 mg of the named compound.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic portion was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88a52a4d05e84387af88cfaa0e38827c
Source dataset
uspto-grants-2002_03
Patent number
US06359181B1

Reaction notes

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