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

HRID 1439007Notes

Reaction equation

HRID 1439007 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 175 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 2 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 ethylacetate 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 2 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 ethylacetate

Sources & evidence

ORD record
ord-7cb45c2af5ff4724b6bb964786042229
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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