L-Phenylalanine → Z-Gly-phe-OH

HRID 1657356Notes

Reaction equation

HRID 1657356 reaction equation
SC1N=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])N=1.[O:10]1CCO[CH2:12][CH2:11]1.SC1N=CC=C[N:18]=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:35]([O:38][CH2:39][CH3:40])(=[O:37])C>[OH-].[Na+]>[NH:18]([C:35]([O:38][CH2:39][C:40]1[CH:9]=[CH:4][CH:5]=[CH:6][CH:8]=1)=[O:37])[CH2:12][C:11]([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:10]

Participants

7

Reactant 5

HCID 6140L-PhenylalanineHCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 178418793HCID 178418793, compoundHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 6998938Z-Gly-phe-OH

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-benzyloxycarbonyl-glycine 4,6-dimethylpyrimidine-2-yl thiolester was synthesized using the same process as described in Example 6 except that 0.005 mole of 2-mercapto-4,6-dimethyl-pyrimidine and 15 ml of dioxane were used instead of 0.01 mole of 2-mercapto-pyrimidine and 50 ml of ethyl acetate. To the obtained reaction solution, 0.99 g (0.006 mole) of L-phenylalanine dissolved in 12 ml of a 0.5 N aqueous solution of sodium hydroxide (L-Phe-ONa) was added and reacted at 20°C for 6 hours. After completion of the reaction, the dioxane was removed by distillation. To the residue, 10 ml of water was added and the resulting solution was washed with ethyl acetate. After adjusting the solution to pH 2 with a 2 N aqueous solution of hydrochloric acid, the resulting solution was extracted with ethyl acetate. The extract was dried over magnesium sulfate and then the solvent was removed by distillation to obtain 1.44 g of Z-Gly-L-Phe-OH; yield, 80 %; m.p. 127° - 127.5°C; [α]D = +37.0 (C=1.0, EtOH).

Workup

  1. additionwas added
  2. customreacted at 20°C for 6 hours
  3. customAfter completion of the reaction
  4. customthe dioxane was removed by distillation
  5. additionTo the residue, 10 ml of water was added
  6. washthe resulting solution was washed with ethyl acetate
  7. extractionthe resulting solution was extracted with ethyl acetate
  8. dry with materialThe extract was dried over magnesium sulfate
  9. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-a61a6f2d09134fbb9ffbd33807823e0c
Source dataset
uspto-grants-1976_06
Patent number
US03960829

Reaction notes

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