Hydrochloric Acid → HCID 11175181, compound

HRID 2118397Notes

Reaction equation

HRID 2118397 reaction equation
COC[O:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21]COC)=[CH:17][CH:16]=3)[CH:9]3[CH2:25][CH:26]([O:28][C:29](=[O:31])[CH3:30])[CH2:27][CH:8]3[C:7]=2[CH:6]=1.Cl.CCOC(C)=O.CCOC(C)=O.CCCCCC>C1COCC1>[OH:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][C@H:10]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[C@@H:9]3[CH2:25][C@H:26]([O:28][C:29](=[O:31])[CH3:30])[CH2:27][C@@H:8]3[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226206Ethyl acetate hexaneHCID 68706056HCID 68706056, compound

Product 1

HCID 11175181HCID 11175181, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve acetate 42 (180 mg, 0.42 mmol) in THF (8 mL) and add 3M HCl (2 mL). Stir the reaction at room temperature overnight. Dilute the reaction with EtOAc and wash with saturated aqueous sodium bicarbonate and brine. Extract the aqueous solutions with EtOAc (1×). Combine, dry (Na2SO4), filter and concentrate the organic solutions in vacuo. Purify the product by flash chromatography (10 g SiO2, dry loading on 700 mg silica, 40 ml/min, 0-50% EtOAc/Hexane over 20 minutes and then 50% EtOAc/hexane for 13 minutes) to afford acetate 43 (47 mg, 0.14 mmol, 33%) as a white solid. The enantiomers were separated.

Workup

  1. customthe reaction at room temperature overnight
  2. additionDilute
  3. washwash with saturated aqueous sodium bicarbonate and brine
  4. extractionExtract the aqueous solutions with EtOAc (1×)
  5. dry with materialCombine, dry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate the organic solutions in vacuo
  8. customPurify the product by flash chromatography (10 g SiO2
  9. dry with materialdry loading on 700 mg silica, 40 ml/min, 0-50% EtOAc/Hexane over 20 minutes

Sources & evidence

ORD record
ord-95965626c3424374a88a9495656957fd
Source dataset
uspto-grants-2008_10
Patent number
US07442812B2

Reaction notes

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