Hydrochloric Acid → HCID 69545714, compound

HRID 1744681Notes

Reaction equation

HRID 1744681 reaction equation
[Mg].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5][CH:4]=1.Cl>CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH:10]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 69546259HCID 69546259, compound

Product 1

HCID 69545714HCID 69545714, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Magnesium metal (1.23 g, 51.0 mmol) was added in three portions over approximately 0.3 h to a stirred solution of the product of step D (1.85 g, 5.1 mmol) in methanol (40 mL) at ambient temperature. After stirring overnight, the reaction mixture was poured into 1 N hydrochloric acid (100 mL) and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–25% ethyl acetate/hexanes as eluent) provided the title compound (mixture of cis/trans diastereoisomers) as a colorless oil (1.5 g).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by medium pressure liquid chromatography on silica gel (gradient elution; 0–25% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-233fa270839347e78b830499fac820ac
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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