Ethylmorpholine → Boc-(D)Ala-Gly-OBzl

HRID 1903865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903865
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([OH:6])=O)[CH3:3].C(N1CCOCC1)C.C(OC(Cl)=O)C(C)C.[CH2:30]([O:37][C:38](=[O:41])[CH2:39][NH2:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O>O1CCCC1.CN(C=O)C>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([NH:40][CH2:39][C:38]([O:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:41])=[O:6])[CH3:3]

Komponenten

7

Edukt 4

HCID 7525Ethylmorpholine2×HCID 62365Isobutyl chloroformateHCID 637606BOC-D-alanineHCID 124082031HCID 124082031, Verbindung

Produkt 1

HCID 15567200Boc-(D)Ala-Gly-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.9 g of Boc-(D)Ala-OH and 1.3 ml of N-ethylmorpholine are dissolved in 50 ml of absolute tetrahydrofuran and 1.3 ml of chloroformic acid iso-butyl ester added dropwise at a temperature of -15°. After 5 minutes, a solution of 3.4 g of glycine-benzylester-tosylate and 1.3 ml of N-ethylmorpholine in 50 ml of DMF is added. After 1 hour's stirring at -10°, the reaction mixture is evaporated and the residue taken up in acetic acid. The solution is repeatedly washed with dilute citric acid and potassium bicarbonate. The title compound is crystallised from ether. M.P. 88°.

Aufarbeitung

  1. customthe reaction mixture is evaporated
  2. washThe solution is repeatedly washed with dilute citric acid and potassium bicarbonate
  3. customThe title compound is crystallised from ether

Quellen und Nachweise

ORD-Eintrag
ord-dc6f42968a364588b273152e97690ea0
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04438103

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