Methanol → HCID 54556555, 화합물

HRID 1734427노트

반응식

HRID 1734427 반응식
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

참가 물질

6

반응물 3

HCID 887MethanolHCID 3246319HCID 3246319, 화합물HCID 86743235HCID 86743235, 화합물

생성물 1

HCID 54556555HCID 54556555, 화합물수율 16.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7e65b9959c7a43f59f57981f25fa9208
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534497

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