Sulfuric acid magnesium salt (1:1) → HCID 90282082, compound

HRID 1497551Notes

Reaction equation

HRID 1497551 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.S([O-])([O-])(=O)=O.[Mg+2].Cl.[NH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>ClCCl>[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 90282082HCID 90282082, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-4-hydroxybenzaldehyde (400 mg) in dichloromethane (4.00 mL) were added anhydrous magnesium sulfate (615 mg) and tert-butyl glycinate hydrochloride (679 mg), followed by stirring at room temperature overnight. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (12.0 mL), and sodium borohydride (193 mg) was added thereto, followed by stirring at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate, and the organic layer was extracted. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain tert-butyl N-(2-chloro-4-hydroxybenzyl)glycinate (613 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (12.0 mL)
  4. additionsodium borohydride (193 mg) was added
  5. stirringby stirring at room temperature for 2 hours
  6. additionTo the reaction mixture were added water and ethyl acetate
  7. extractionthe organic layer was extracted
  8. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b531f84d214c437d8452795e8515c915
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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