Sodium Carbonate → N-benzyloxycarbonylphenylalanine methyl ester

HRID 565089Notes

Reaction equation

HRID 565089 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 3082435N-benzyloxycarbonylphenylalanine methyl esterYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.0 g (92.73 mmol) of (L)-phenylalanine methyl ester hydrochloride was suspended in 93 ml of toluene, and 15.82 g (92.73 mmols) of benzyl chloroformate was added thereto. 130 ml of an aqueous solution of 1 M sodium carbonate was dropwise added thereto, while keeping it at 7° C. or lower, and stirred for 3 hours. After this was subjected to phase separation, the resulting organic layer was washed with 60 ml of 0.1 N hydrochloric acid and 60 ml of a saturated aqueous solution of sodium hydrogen carbonate, and then dried with anhydrous sodium sulfate. This was filtered and concentrated to obtain 28.75 g (96.8 wt. %, 88.81 mmol) of the above-entitled compound. The yield was 95.8%.

Workup

  1. customat 7° C.
  2. customAfter this was subjected to phase separation
  3. washthe resulting organic layer was washed with 60 ml of 0.1 N hydrochloric acid and 60 ml of a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationThis was filtered
  6. concentrationconcentrated
  7. customto obtain 28.75 g (96.8 wt. %, 88.81 mmol) of the above-entitled compound

Sources & evidence

ORD record
ord-d99a4845f4c746fe86512a41539fc31a
Source dataset
uspto-grants-2001_01
Patent number
US06169200A

Reaction notes

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