Water → HCID 61137645, compound

HRID 2369754Notes

Reaction equation

HRID 2369754 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3].N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].O>C(Cl)Cl>[C:24]([NH:1][CH:2]([CH3:3])[C:4]([NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 96814L-alanyl-L-phenylalanine

Product 1

HCID 61137645HCID 61137645, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Ala-L-Phe obtained in Experimental Example 6 (100 mg, 0.423 mmol) is suspended in methylene chloride (10 ml), and pyridine (10 ml) and acetic anhydride (1 ml, 11 mmol) are added to the suspension at room temperature. After stirring at room temperature for 24 hours, water is added and the resulting mixture is extracted three times with chloroform. The organic layer is washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled away under reduced pressure to obtain N-[2-(acetylamino)propionyl]phenylalanine.

Workup

  1. extractionthe resulting mixture is extracted three times with chloroform
  2. washThe organic layer is washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled away under reduced pressure

Sources & evidence

ORD record
ord-fc50ba2ed0ec4b93b3a3ab5178e08edd
Source dataset
uspto-grants-2014_04
Patent number
US08709752B2

Reaction notes

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