p-Anisoyl chloride → methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate

HRID 839941Notes

Reaction equation

HRID 839941 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([NH:13][C@H:14]([C:23]([O:25][CH3:26])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:33][O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>O.C(Cl)(Cl)Cl>[CH3:33][O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH:2][C@H:3]([C:11]([NH:13][C@H:14]([C:23]([O:25][CH3:26])=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[O:12])[CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:40])=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 10340Sodium Carbonate2×HCID 70615103Methyl phenylalanyltyrosinate hydrochloride

Product 1

HCID 53971131methyl N-(4-methoxybenzoyl)phenylalanyltyrosinateYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

In a mixture of 10 ml of water and 50 ml of chloroform were suspended 3.79 g of methyl phenylalanyltyrosinate hydrochloride and 0.53 g of sodium carbonate. To the mixture was added dropwise 1.75 g of 4-methoxybenzoylchloride in parallel with 10 ml of sodium carbonate solution (0.75 g), while stirring and cooling with ice. The mixture was stirred for two hours and the chloroform layer was collected. The layer was washed with 5% hydrochloric acid and water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 3.9 g of methyl N-(4-methoxybenzoyl)-phenylalanyltyrosinate with a mp. 195°-197° C in a yield of 82%. Analysis, calculated for C27H28O6N2C 68.05, H 5.92, N 5.88, found C 68.42, H 6.08, N 5.74.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture was stirred for two hours
  3. customthe chloroform layer was collected
  4. washThe layer was washed with 5% hydrochloric acid and water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-60e35d66316d400f8427b127e290cfce
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

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