Citric Acid → HCID 14336499, Verbindung

HRID 373392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373392
O.[C:2]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:29]([O:36][C:37](=[O:43])[C@H:38]([CH:40]([CH3:42])[CH3:41])[NH2:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl(O)(=O)(=O)=O.C(N=C=NCCCN(C)C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.O>[CH2:29]([O:36][C:37](=[O:43])[C@H:38]([CH:40]([CH3:41])[CH3:42])[NH:39][C:15](=[O:17])[C@@H:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[NH:9][C:2]([O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:3])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

9

Edukt 6

HCID 311Citric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2724763D-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-, monohydrateHCID 11567066O-benzyl-L-valine toluene-p-sulphonateHCID 18959840HCID 18959840, Verbindung

Produkt 1

HCID 14336499HCID 14336499, VerbindungAusbeute 110,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.749 g (3.00 mmol) of Boc-D-leucine monohydrate, 1.252 g (3.30 mmol) of L-valine benzyl ester p-toluenesulfonate and 0.811 g (6.00 mmol) of N-hydroxybenzotriazole were dissolved in 15 ml of dichloromethane. The resulting mixture was cooled with ice, and admixed with 0.504 ml (3.60 mmol) of triethylamine and 1.108 g (4.20 mmol) of 97% 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide perchlorate. The reaction mixture was stirred for 2 hours, and then further stirred at room temperature for 4 hours. After the completion of the reaction, 30 ml of water and 5 ml of a 1% aqueous citric acid solution were added to the reaction mixture. The crystals thus deposited were filtered off. The organic layer successively was washed with 20 ml of water, 20 ml of a saturated aqueous sodium hydrogen carbonate solution and 10 ml of water, dried over anhydrous sodium sulfate, and distilled to remove the solvent therefrom, whereby 1.390 g of crude Boc-D-leucyl-L-valine benzyl ester product were obtained as white crystals.

Aufarbeitung

  1. temperatureThe resulting mixture was cooled with ice
  2. stirringfurther stirred at room temperature for 4 hours
  3. additionwere added to the reaction mixture
  4. filtrationThe crystals thus deposited were filtered off
  5. washThe organic layer successively was washed with 20 ml of water, 20 ml of a saturated aqueous sodium hydrogen carbonate solution and 10 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-c2907bbe056e4674bccabd51ce6b7734
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162500

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