691-81-6 → HCID 53778955, compound

HRID 2082115Notes

Reaction equation

HRID 2082115 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@@H:6]([C:8]([OH:10])=[O:9])[CH3:7])=[O:4].[C:11]1(=[O:34])[N:15]([N:16]([C:21](=[O:32])[CH2:22][S:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][C:18]([O-:20])=[O:19])[C:14](=[O:33])[CH2:13][CH2:12]1>O.C(O)C>[C:14]1(=[O:33])[N:15]([N:16]([C:21](=[O:32])[CH2:22][S:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][C:18]([O-:20])=[O:19])[C:11](=[O:34])[CH2:12][CH2:13]1.[C:24]([S:23][CH2:22][C:21]([NH:1][CH2:2][C:3]([NH:5][C@@H:6]([C:8]([OH:10])=[O:9])[CH3:7])=[O:4])=[O:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 2

HCID 11966077691-81-62×HCID 86743235HCID 86743235, compound

Product 2

HCID 53778955HCID 53778955, compoundYield 31.6%HCID 86743235HCID 86743235, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Succinimidyl-N-(S-benzoylmercaptoacetyl)glycinate is prepared according to the method described by R. F. Schneider et al, Journal of Nuclear Medicine 25 (2), 223-229 (1984). Glycyl-D-alanine in an amount of 250 mg is dissolved in 15 ml of water and the mixture is heated to 70° C. on a water bath. Meanwhile, 1 g of succinimidyl-N-(S-benzoylmercaptoacetyl)glycinate is dissolved in 40 ml of ethanol and the mixture is heated to 70° C. on a water bath. The solution of glycyl-D-alanine in water is added at once to the said ethanolic solution while stirring magnetically. The mixture is then refluxed for 1 hour. After cooling, the solution is evaporated to dryness under reduced pressure. The solid residue is shaken five times with 15 ml of acetone which is each time filtered off. Benzoylmercaptoacetylglycyl-D-alanine is precipitated from the collected filtrates by the addition of diethylether. The precipiate is filtered off and dried in vacuo over phosphorous pentoxide. In this manner 174 mg (yield 31.6%) of benzoylmercaptoacetylglycyl-D-alanine are obtained as a white crystalline powder.

Workup

  1. temperaturethe mixture is heated to 70° C. on a water bath
  2. temperatureThe mixture is then refluxed for 1 hour
  3. temperatureAfter cooling
  4. customthe solution is evaporated to dryness under reduced pressure
  5. stirringThe solid residue is shaken five times with 15 ml of acetone which
  6. filtrationfiltered off
  7. customBenzoylmercaptoacetylglycyl-D-alanine is precipitated from the collected filtrates by the addition of diethylether
  8. filtrationThe precipiate is filtered off
  9. dry with materialdried in vacuo over phosphorous pentoxide

Sources & evidence

ORD record
ord-c2e49d63fb964befa8c99f33224e74c1
Source dataset
uspto-grants-1993_02
Patent number
US05187264

Reaction notes

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