Methanol → HCID 54556555, compound

HRID 1734427Notes

Reaction equation

HRID 1734427 reaction equation
C1(=O)N([N:6]([C:11](=[O:22])[CH2:12][S:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][C:8]([O-:10])=O)C(=O)CC1.[NH2:25][C@@H:26]([C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[CH2:27][OH:28].CO>C(O)C.O>[C:14]([S:13][CH2:12][C:11]([NH:6][CH2:7][C:8]([NH:25][C@@H:26]([C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[CH2:27][OH:28])=[O:10])=[O:22])(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3246319HCID 3246319, compoundHCID 86743235HCID 86743235, compound

Product 1

HCID 54556555HCID 54556555, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6.4 g succinimidyl-N-(S-benzoylmercaptoacetyl)glycinate in 40 ml of ethanol at ? 0° C. is added in one portion a solution of 1.008 g of the above D-serylglycine in 10 ml of water at 70° C. The reaction mixture is refluxed for i hour and then stirred at room temperature overnight. After evaporation of the solvents the residue is agitated with 25 ml of acetone. The precipitate is removed by filtration. Diethylether is added to the filtrate until precipitation is complete. The precipitate is collected by filtration and washed with diethylether. After drying 1.56 g of a yellowish powder is obtained. To 600 mg of this is added 15 ml of chilled methanol. After agitation during 5 min. the white precipitate is filtered off, washed with cold methanol and dried to obtain 400 mg of S-benzoylmercaptoacetylglycyl-D-serylglycine as a white powder, m.p. 149° C. N.M.R. (DMSO-d6):δ3.61 (2H, d, CH2 --OH), 3.77 (2H, d, α--CH2 --N), 3.84 (2H, d,β--CH2 --N), 3.88 (2H, s, S--CH2), 4.38 (1H, dr, CH), 8.03 (1H, d,β--NH), 8.17 (1H, t,α--NH), 8.44 (1H, t,γ--NH).

Workup

  1. temperatureThe reaction mixture is refluxed for i hour
  2. customAfter evaporation of the solvents the residue
  3. stirringis agitated with 25 ml of acetone
  4. customThe precipitate is removed by filtration
  5. additionDiethylether is added to the filtrate until precipitation
  6. filtrationThe precipitate is collected by filtration
  7. washwashed with diethylether
  8. dry with materialAfter drying 1.56 g of a yellowish powder
  9. customis obtained
  10. filtrationAfter agitation during 5 min. the white precipitate is filtered off
  11. washwashed with cold methanol
  12. customdried

Sources & evidence

ORD record
ord-7e65b9959c7a43f59f57981f25fa9208
Source dataset
uspto-grants-1996_07
Patent number
US05534497

Reaction notes

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