Pyridine → 2768-53-8

HRID 1759505Notes

Reaction equation

HRID 1759505 reaction equation
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].N1C=CC=CC=1.[NH2:23][C@H:24]([C:32]([OH:34])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@H:2]([C:4]([NH:23][C@H:24]([C:32]([OH:34])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 736104N-carbobenzyloxyalanine2×

Product 1

HCID 69991262768-53-8Yield 72.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.223 g (0.001 mol) of Z-Ala, 0.08 g (0.001 mol) of pyridine and 0.256 g (0.001 mol) of DSC in 10 ml of DMF was stirred at ambient temperature. After silica gel TLC. showed that Z-Ala disappeared in the solution, the reaction solution was admixed with a solution of 0.165 g (0.001 mol) of phenylalanine (Phe-OH) and 0.101 g (0.001 mol) of triethylamine in 20 ml of DMF. After 24 hours, the reaction mixture was admixed with ethyl acetate, washed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride, followed by drying over anhydrous sodium sulfate. The dried reaction solution was filtered and the filtrate was distilled to remove the solvent, affording a colorless crystalline substance. Recrystallization of this crystalline substance from methylene chloride-ethyl ether gave 0.27 g of Z-Ala-Phe-OH in the form of a colorless crystalline substance. Yield 72%.

Workup

  1. washwashed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customThe dried reaction solution
  4. filtrationwas filtered
  5. distillationthe filtrate was distilled
  6. customto remove the solvent
  7. customaffording a colorless crystalline substance
  8. customRecrystallization of this crystalline substance from methylene chloride-ethyl ether

Sources & evidence

ORD record
ord-e5194cbcda844572bf4bbd48a372ecf3
Source dataset
uspto-grants-1982_07
Patent number
US04341707

Reaction notes

Loading…