Diethyl Ether → HCID 54320917, Verbindung

HRID 231871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231871
C1(=O)N(N([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)CC([O-])=O)C(=O)CC1.[NH2:25][C@@H:26]([C:28]([NH:30][CH2:31][C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])=[O:29])[CH3:27].C(OCC)C>C(O)C.O>[C:14]([S:13][CH2:12][C:11]([NH:25][C@@H:26]([C:28]([NH:30][CH2:31][C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])=[O:29])[CH3:27])=[O:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 154942777286-90-9HCID 86743235HCID 86743235, Verbindung

Produkt 1

HCID 54320917HCID 54320917, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1 g of succinimidyl-N-(S-benzoylmercaptoacetyl)glycinate in 25 ml of anhydrous ethanol at 70° C. is added in one portion a solution of 203 mg of D-alanylglycylglycine in 10 ml of water at 70° C. The reaction mixture is refluxed for 1 hour and the solvents are evaporated under reduced pressure. The residue is agitated with 5 portions of 25 ml acetone, which is isolated by filtration. The combined filtrates are treated with diethylether until precipitation is complete. The precipitate is filtered off, washed with diethylether and dried over P2O5 under vacuum to obtain 170 mg (47,7%) of S-benzoylmercaptoacetyl-d-alanylglycylglycine as a white powder, m.p. 167°-170° C. [α]D20 +22 (c=1 in methanol); nmr (DMSO-d6): δ 1.24 (3H, d, CH3), 3.88 (2H, s, CH2 --S), 3.74 (4H, d, 2×CH2 --N), 4.31 (1H, q, CH), 8.08 and 8.24 (each 1H, t, α-- and β--NH), 8.51 (1H, d, δ--NH), 7.5-8.04 (5H, complex, aromatic).

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. customthe solvents are evaporated under reduced pressure
  3. customwhich is isolated by filtration
  4. filtrationThe precipitate is filtered off
  5. washwashed with diethylether
  6. dry with materialdried over P2O5 under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c692cea4e0af41ec8901ffad7793eb23
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849511

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