Hydrochloric Acid → N-(4-methoxybenzoyl)-phenylalanyltyrosine

HRID 1439008Notes

Reaction equation

HRID 1439008 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:22]([OH:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.Cl>[OH-].[Na+]>[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:1][C@H:2]([C:10]([NH:12][C@H:13]([C:22]([OH:24])=[O:23])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[O:11])[CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 515709Phe-Tyr

Product 1

HCID 54084741N-(4-methoxybenzoyl)-phenylalanyltyrosineYield 56.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

In 20 ml of 1N sodium hydroxide solution, 3.28 g of phenylalanyltyrosine was dissolved and the solution was cooled with ice. To the cold solution were added dropwise 1.7 g of 4-methoxybenzoylchloride and 10 ml of 1N sodium hydroxide solution. After stirring for 2 hours, the mixture was neutralized with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 2.6 g of N-(4-methoxybenzoyl)-phenylalanyltyrosine in a yield of 56%.

Workup

  1. temperaturethe solution was cooled with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-730a6d8d9b904f4996e0ab14cea922e5
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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