L-Phenylalanine → Z-Gly-phe-OH

HRID 1462152Notes

Reaction equation

HRID 1462152 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ON1C2C=CC=CC=2N=N1.ClC1C=CC([O:30][C:31](=O)[CH2:32][NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])=C(Cl)C=1Cl.C(N1CCOCC1)C>CN(C)C=O>[CH2:37]([O:36][C:34]([NH:33][CH2:32][C:31]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:30])=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 6140L-PhenylalanineHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 20453969HCID 20453969, compound

Product 1

HCID 6998938Z-Gly-phe-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.5 g of phenylalanine are suspended in 150 ml of dimethylformamide (DMF), 13.5 g of 1-hydroxybenzotriazole, 38.8 g of benzyloxycarbonylglycine-trichlorophenyl ester and 12.8 ml of N-ethylmorpholine are added and the batch is stirred for 8 hours at room temperature. The product is concentrated in vacuo, dissolved in 1 liter of ethyl acetate and submitted to repeated extractions with200ml portions of 2 N citric acid and of saturated sodium chloride solution, respectively. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue crystallizes from ethyl acetate/diisopropyl ether.

Workup

  1. concentrationThe product is concentrated in vacuo
  2. dissolutiondissolved in 1 liter of ethyl acetate
  3. extractionextractions with200ml portions of 2 N citric acid
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue crystallizes from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-6f32b92dab35476789dad0a909b2ab2a
Source dataset
uspto-grants-1984_07
Patent number
US04459225

Reaction notes

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