Water → Boc-L-phenylalanine methyl ester

HRID 1862597Notes

Reaction equation

HRID 1862597 reaction equation
O.Cl.[CH3:3][O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7].[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+]>CO>[CH3:3][O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:7][C:16]([O:17][C:9]([CH3:14])([CH3:10])[CH3:8])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 9882138Boc-L-phenylalanine methyl esterYield 188.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

To a mixed solvent of methanol (50 ml) and water (100 ml) were added L-phenylalanine methyl ester hydrochloride (21.6 g), sodium carbonate (11.64 g), and a solution of di-tert-butoxydicarbonate (21.8 g) in methanol (100 ml). The resulting mixture was heated to 40° C., followed by stirring for 6 hours. The reaction mixture was concentrated to remove the methanol. The concentrate was extracted by adding ethyl acetate and water. The resulting ethyl acetate layer was washed with 0.1 N hydrochloric acid, water, an aqueous sodium hydrogencarbonate solution and a saturated solution of sodium chloride. The ethyl acetate layer after washed was dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off. The solvent was distilled off under reduced pressure to give the target N-tert-butoxycarbonyl-L-phenylalanine methyl ester (26.4 g) in a yield of 95%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the methanol
  3. extractionThe concentrate was extracted
  4. additionby adding ethyl acetate and water
  5. washThe resulting ethyl acetate layer was washed with 0.1 N hydrochloric acid, water
  6. washThe ethyl acetate layer after washed
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationThe magnesium sulfate was filtered off
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1f30a955cc424be18070ba38559b0a28
Source dataset
uspto-grants-2003_03
Patent number
US06538160B2

Reaction notes

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