L-Phenylalanine → (2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]-3-phenylpropanoic acid

HRID 596208Notes

Reaction equation

HRID 596208 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].[CH3:18][O:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][O:25][C:26](ON=C(C(OCC)=O)C(OCC)=O)=[O:27])=[CH:22][CH:21]=1>O.C(O)(C)(C)C>[CH3:18][O:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][O:25][C:26]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 6140L-PhenylalanineHCID 516892Sodium Bicarbonate2×HCID 13305521HCID 13305521, compound

Product 1

HCID 11823666(2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]-3-phenylpropanoic acidYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 6386tert-ButanolSolvent

Procedure

L-Phenylalanine (330 mg.) and sodium bicarbonate (202 mg.) were dissolved in water (10 ml.) with heating and allowed to stand. To the solution was added a solution of diethyl 2-(4-methoxybenzyloxycarbonyloxyimino)malonate (1.0 g.) in tert-butyl alcohol (10 ml.) with stirring at room temperature and water (10 ml.) was added thereto, after which the mixture was stirred for 2 hours at room temperature. The reaction mixture was brought to pH 9 by adding water (20 ml.) and a saturated sodium bicarbonate aqueous solution (10 ml.), and water (10 ml.) was added thereto, after which the mixture was washed twice with ethyl acetate (20 ml.). The aqueous layer was adjusted to pH 7 with a 10% citric acid aqueous solution, washed twice with ethyl acetate (30 ml.), adjusted to pH 3.5 with a 10% citric acid aqueous solution and extracted three times with ethyl acetate (30 ml.). The extract was washed with a sodium chloride aqueous solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give N-(4-methoxybenzyloxycarbonyl)-L-phenylalanine (410 mg.), oil.

Workup

  1. temperaturewith heating
  2. stirringafter which the mixture was stirred for 2 hours at room temperature
  3. washafter which the mixture was washed twice with ethyl acetate (20 ml.)
  4. washwashed twice with ethyl acetate (30 ml.)
  5. extractionextracted three times with ethyl acetate (30 ml.)
  6. washThe extract was washed with a sodium chloride aqueous solution
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-76f0bdc2e3cc4024a72fda03d7a1172e
Source dataset
uspto-grants-1977_03
Patent number
US04010178

Reaction notes

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