4-Methylmorpholine → N-Cbz-5-hydroxy-L-norvaline methyl ester

HRID 556389

Reaktionsgleichung

Reaktionsgleichung von HRID 556389
[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:8]([O:10][CH3:11])=[O:9])[CH2:3][CH2:4][C:5](=O)[OH:6].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.CO>[CH3:11][O:10][C:8](=[O:9])[C@@H:2]([NH:1][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH2:3][CH2:4][CH2:5][OH:6]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2733408(4S)-4-{[(benzyloxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acidHCID 4311764Sodium borohydride

Produkt 1

HCID 10588891N-Cbz-5-hydroxy-L-norvaline methyl esterAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a cold (−15° C.) solution of Cbz-Glu-OMe (1.5 g) in THF (70 mL) was added N-methylmorpholine (0.616 mL) followed by isobutyl chloroformate (0.731 mL) dropwise. After 30 min stirring at −15° C., NaBH4 (576 mg) was added, followed MeOH dropwise. The reaction mixture was stirred at −10° C. for 15 min and quenched by the addition of 1M KHSO4 solution. The mixture was extracted with EA. The org. phase was washed with water, dried (Na2SO4) and evaporated off to give the crude product as a colourless oil (1.5 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at −10° C. for 15 min
  2. customquenched by the addition of 1M KHSO4 solution
  3. extractionThe mixture was extracted with EA
  4. washphase was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated off

Quellen und Nachweise

ORD-Eintrag
ord-4f1ce3f10b7442eba7e321d9768f01b5
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058263B2

Verknüpfte Notizen

Wird geladen…