4-Methylmorpholine → HCID 131723142, Verbindung

HRID 277676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277676
[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([NH:11][C@H:12]([C:14](O)=[O:15])[CH3:13])=[O:10])[CH3:8])=[O:5])[CH3:3].CN1CCOCC1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CN(C=O)C.O>[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([NH:11][C@H:12]([CH2:14][OH:15])[CH3:13])=[O:10])[CH3:8])=[O:5])[CH3:3]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 14459756N-[(Benzyloxy)carbonyl]-L-alanyl-L-alanyl-L-alanine

Produkt 1

HCID 131723142HCID 131723142, VerbindungAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 5 g (0.014 mol) of Z-Ala-Ala-AlaOH dissolved in THF/DMF 1:1 (50 mL) at −10° C. under a N2 atmosphere were added 1.6 mL (0.014 mol) NMM and 1.9 mL (0.014 mol) IBCF. The reaction mixture was stirred 15 minutes, filtered, and the filtrate added slowly to an ice-cold solution of NaBH4 (1.4 g, 0.037 mol) in H2O (3 mL) and stirred 1 hour at ice-bath temperature and 1 hour at room temperature. The reaction mixture was cooled to 0° C. and treated with saturated NaHCO3 solution, extracted with EtOAc, washed with 1M HCl that is saturated with NaHCO3, dried over anhydrous MgSO4, and evaporated to dryness. The crude product was purified over a silica gel column eluted with 95:5 EtOAc/MeOH to give 1.2 g product.

Aufarbeitung

  1. filtrationfiltered
  2. stirringstirred 1 hour at ice-bath temperature and 1 hour at room temperature
  3. extractionextracted with EtOAc
  4. washwashed with 1M HCl that
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated to dryness
  7. customThe crude product was purified over a silica gel column
  8. washeluted with 95:5 EtOAc/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-ce4eb2239e484af88531f03b00f1e384
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358928B1

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