Water → N-Acetyl-L-phenylalanine

HRID 1647014Notes

Reaction equation

HRID 1647014 reaction equation
O.[C:2](OC(=O)C)(=[O:4])[CH3:3].[NH2:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:2]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 3

HCID 962WaterHCID 6140L-PhenylalanineHCID 7918Acetic Anhydride

Product 1

HCID 74839N-Acetyl-L-phenylalanineYield 71%

Procedure

In 15 ml of water 8.26 g (50 mmol) of phenylalanine were dissolved. While vigorously stirring this aqueous solution, 10.2 g (100 mmol) of acetic anhydride were added thereto. After the exothermic reaction had been completed, the reaction mixture was further stirred for about 30 minutes and allowed to stand in a refrigerator for about 24 hours. The precipitates thus formed were filtered, washed with water and dried to obtain 7.4 g (yield: 71 %) of N-acetyl-phenylalanine. Then, 1.18 g (5.7 mmol) of this N-acetylphenyl-alanine were dissolved in a solution of 580 mg (5.7 mmol) of triethylamine dissolved in 30 ml of anhydrous tetrahydrofuran. While cooling the resulting solution in an ice bath, 690 mg (5.7 mmol) of pivalyl chloride were added thereto and the mixture was stirred for about 2 hours. To the resulting mixture was added a solution of 820 mg (5.7 mmol) of 8-aminoquinoline dissolved in 10 ml of tetrahydrofuran and the mixture was stirred for about 24 hours. After being added with chloroform, the resulting mixture was washed with a saturated sodium bisulfate solution and then with water, and dried over anhydrous sodium sulfate, followed by distillation in vacuo for the removal of the solvent. The residue was then subjected to column chromatography to obtain 890 mg of a product with a yield of 47%. The NMR, IR and MS spectra reveal that this product is 8-(N-acetylphenylalanylamino)quinoline of the formula (I) in which R1 is metyl and R2 is benzyl. The mass analysis shows:

Workup

  1. additionwere added
  2. customAfter the exothermic reaction
  3. waitto stand in a refrigerator for about 24 hours
  4. customThe precipitates thus
  5. customformed
  6. filtrationwere filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f16257f729bf4a09b73ac26e76019fdf
Source dataset
uspto-grants-1993_01
Patent number
US05182398

Reaction notes

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