Hydrochloric Acid → HCID 178501252, compound

HRID 2373697Notes

Reaction equation

HRID 2373697 reaction equation
C[O-].[Na+].C(OC)=O.[CH3:8][C:9]([S:12]([NH:15][C@@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)(=[O:14])=[O:13])([CH3:11])[CH3:10].Cl>C1(C)C=CC=CC=1>[CH3:11][C:9]([S:12]([NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)(=[O:14])=[O:13])([CH3:8])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 10942334Sodium MethoxideHCID 178501251HCID 178501251, compound

Product 1

HCID 178501252HCID 178501252, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of powder sodium methylate (7.06 g, 2.5 eq) in toluene (145 mL) was added methyl formate (1.61 mL, 0.5 eq). After the mixture was stirred for an hour at room temperature, (15) (14.5 g, 52.3 mmol) was added to the mixture. The mixture was heated under reflux for 2 hours 25 minutes, cooled and poured into 0.76 mol/L hydrochloric acid (344 mL). The mixture was extracted with ethyl acetate (300 mL×2), and the obtained organic layer was washed with water and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure to obtain 14.42 g of crystalline residue (cis:trans=3:97). The residue was recrystallized from toluene to obtain (12) (10.2 g, 70% from (15)).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours 25 minutes
  3. temperaturecooled
  4. extractionThe mixture was extracted with ethyl acetate (300 mL×2)
  5. washthe obtained organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-998b9bafc006409fa319441fdf788d9c
Source dataset
uspto-grants-2008_12
Patent number
US07459580B2

Reaction notes

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