Hydrochloric Acid → N-Acetyl-L-phenylalanine

HRID 1197217Notes

Reaction equation

HRID 1197217 reaction equation
COS([O-])(=O)=O.C[S+](C)C1C=CC([CH2:15][C:16](O)=[O:17])=CC=1.[NH2:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl>O>[C:16]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:17])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 88483146HCID 88483146, compound

Product 1

HCID 74839N-Acetyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 30 ml of water was dissolved 3.1 g of p-dimethylsulfoniophenylacetate methylsulfate prepared in Synthetic Example 3, and 20 ml of an aqueous solution of 1.64 g of phenylalanine and 1.4 ml of triethylamine was dropwise added thereto under stirring at room temperature. The reaction mixture was further stirred for 12 hours at room temperature and adjusted to pH 2 by adding 2% HCl. The aqueous solution was extracted twice with 50 ml of ethyl acetate. The ethyl acetate layer was washed with water, dried, and concentrated under reduced pressure, and ether was added to the obtained residue to afford a white crystalline product.

Workup

  1. additionwas dropwise added
  2. stirringThe reaction mixture was further stirred for 12 hours at room temperature
  3. extractionThe aqueous solution was extracted twice with 50 ml of ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure, and ether
  7. additionwas added to the obtained residue
  8. customto afford a white crystalline product

Sources & evidence

ORD record
ord-a202b34374b4407080e6549ab1afcf7f
Source dataset
uspto-grants-1992_05
Patent number
US05117031

Reaction notes

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