Hydrochloric Acid → HCID 11404175, compound

HRID 2118395Notes

Reaction equation

HRID 2118395 reaction equation
[CH3:1][O:2][CH:3]1[CH2:29][CH:6]2[CH:7]([C:19]3[CH:24]=[CH:23][C:22]([O:25]COC)=[CH:21][CH:20]=3)[O:8][C:9]3[CH:10]=[CH:11][C:12]([O:15]COC)=[CH:13][C:14]=3[CH:5]2[CH2:4]1.Cl.CCOC(C)=O.CCOC(C)=O.CCCCCC>C1COCC1>[OH:25][C:22]1[CH:21]=[CH:20][C:19]([C@@H:7]2[C@@H:6]3[CH2:29][C@H:3]([O:2][CH3:1])[CH2:4][C@@H:5]3[C:14]3[CH:13]=[C:12]([OH:15])[CH:11]=[CH:10][C:9]=3[O:8]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226206Ethyl acetate hexaneHCID 68703551HCID 68703551, compound

Product 1

HCID 11404175HCID 11404175, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve methyl ether 40 (205 mg, 0.51 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 the organic solutions, dry (Na2SO4), filter and concentrate them 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 methyl ether 41 (125 mg, 0.4 mmol,78%) as a white solid. HRMS(ES+) calcd for C19H23NO4: 330.1705; found: 330.1695 (M+NH4); HPLC (Zorbax C18 column; 10 to 100% CH3CN/H2O for 10 min then 100% CH3CN for 5 min; 1 mL/min; tr 8.95 min). The enantiomers wre separated by preparative chiral chromatography, chiralpol AD, IPA/Heptane.

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 the organic solutions, dry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate them 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-40dca5db00e64710b246303c5ea9f396
Source dataset
uspto-grants-2008_10
Patent number
US07442812B2

Reaction notes

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