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

HRID 2082979Notes

Reaction equation

HRID 2082979 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]([O:11]N=C(C2C=CC=CC=2)C#N)=O)=[CH:5][CH:4]=1.[NH2:24][C@H:25]([C:33]([OH:35])=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.O1CCOCC1>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([NH:24][C@H:25]([C:33]([OH:35])=[O:34])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:11])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 39162272-(4-Methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 11823666(2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]-3-phenylpropanoic acidYield 64.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(4-Methoxybenzyl)oxycarbonyloxyimino-2-phenylacetonitrile (1.55 g.) was added to a solution of L-phenylalanine (826 mg.) and triethylamine (0.75 ml.) in a mixture of methanol (10 ml.), dioxane (1.5 ml.) and water (7.5 ml.) at room temperature. The resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated, and benzene and a sodium bicarbonate aqueous solution were added to the residue. After shaking the resultant mixture, the aqueous layer was separated from the mixture, washed with ether, acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. N-Hexane was added to the residue and the precipitated crystals were collected by filtration and dried to give N-(4-methoxybenzyl)oxycarbonyl-L-phenylalanine (1.064 g.), mp 87° to 88° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionbenzene and a sodium bicarbonate aqueous solution were added to the residue
  3. stirringAfter shaking the resultant mixture
  4. customthe aqueous layer was separated from the mixture
  5. washwashed with ether
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated
  10. additionN-Hexane was added to the residue
  11. filtrationthe precipitated crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-1dea01b930b94894a3816473d2be000b
Source dataset
uspto-grants-1978_04
Patent number
US04083848

Reaction notes

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