4-Methylmorpholine → Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

HRID 2356036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356036
[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C@@H:2]([C:15](O)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC.O>[CH:24]1[C:23]2[CH:22]([CH2:21][O:20][C:18]([NH:1][C@@H:2]([CH2:15][OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:19])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 13585941(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

Produkt 1

HCID 11655404Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A solution of Fmoc-D-Lys(BOC)-OH (2.102 g, 4.5 mmol) in DME (5 mL) at −15° C. was treated successively with N-methylmorpholine (0.56 mL, 5.0 mmol) and isobutyl chloroformate (0.7 mL, 5 mmol), stirred for 2 minutes, and filtered. The filter cake was washed with DME (3×5 mL) and the combined filtrate and washings were cooled to −5° C. and treated with NaBH4 (0.3 g, 7.5 mmol) in water (5 mL) and additional water (250 mL) immediately afterwards. The mixture was stirred for 15 minutes and filtered. The filter cake was washed with water and dried to provide the desired product. MS (APCI) m/e 455 (M+H)+.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filter cake was washed with DME (3×5 mL)
  3. stirringThe mixture was stirred for 15 minutes
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-290cb8c61e834c27bf0520d9dcd562c0
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754886B2

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