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Water → HCID 58319584, Verbindung

HRID 929896
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 929896
[C:1]([O:5][C:6]([C@:8]1([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][C@H:12]([OH:14])[C@@H:11]2[C@H:9]1[C@H:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.S([O-])(O)(=O)=O.[K+].O>CN(C)C1C=CN=CC=1.ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([C@:8]1([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][C@H:12]([O:14][S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=2)(=[O:38])=[O:37])[C@@H:11]2[C@H:9]1[C@H:10]2[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 516920Potassium bisulfateHCID 59712892ditert-butyl(1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Produkt 1

HCID 58319584HCID 58319584, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 8471TriethylamineKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Charge a 2-necked round bottom flask under nitrogen atmosphere with ditert-butyl(1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (20.7 g, 0.5 mol, see WO03/104217/A2 for synthesis details), 4-dimethylaminopyridine (10.4 g, 0.85 mol), triethylamine (6.98 mL, 0.5 mmol) and p-toluenesulfonyl chloride (10.6 g, 0.55 mol) in dichloromethane (200 mL), and stir the mixture at room temperature overnight. Add 1N solution of potassium hydrogen sulfate (200 mL), water (100 mL) and extract the organic layer. Wash with water (200 mL), brine (200 mL), dry over magnesium sulfate, filter and evaporate to dryness. Add tetrahydrofuran (30 mL) then heptanes (90 mL). Heat the mixture at 60° C. and slowly add more heptanes (200 mL). Cool the mixture to room temperature. Filter the solid and dry under reduced pressure to yield the title compound as a white solid (24.6 g, 87%). MS (m/z): 590 (M+23).

Aufarbeitung

  1. extractionextract the organic layer
  2. washWash with water (200 mL), brine (200 mL)
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. customevaporate to dryness
  6. temperatureHeat the mixture at 60° C.
  7. additionslowly add more heptanes (200 mL)
  8. temperatureCool the mixture to room temperature
  9. filtrationFilter the solid
  10. customdry under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06942330eb844b6f89b4a355fd33113c
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296710B2

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