Acetic Acid → HCID 29949005, compound

HRID 1951916Notes

Reaction equation

HRID 1951916 reaction equation
Cl.[C:2]([O:6][CH2:7][C@@H:8]([C:10]([O:12][CH3:13])=[O:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(O)(=O)C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([BH3-])#N.[Na+]>CO>[CH2:18]([NH:9][C@H:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:6][C:2]([CH3:5])([CH3:4])[CH3:3])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16218549Methyl O-tert-butyl-L-serinate--hydrogen chloride (1/1)

Product 1

HCID 29949005HCID 29949005, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl O-tert-butyl-L-serinate hydrochloride (12 g, 56.7 mmol) was dissolved in methanol (120 ml), acetic acid (6.50 ml, 114 mmol), benzaldehyde (6.25 ml, 61.8 mmol), and sodium cyanoborohydride (1 M tetrahydrofuran solution, 75 ml) were added and the resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated, diluted with water, and neutralized with sodium bicarbonate under ice cooling, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, then the drying agent was removed by filtration and the solvent was concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography [ethyl acetate:n-hexane=1:4 (v/v)] to give the title compound (7.75 g, 52%) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe drying agent was removed by filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel chromatography [ethyl acetate:n-hexane=1:4 (v/v)]

Sources & evidence

ORD record
ord-7b9568e19fb24b11bc8295b304ac2f55
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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