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Sodium Azide → (S)-2'-azido-7'-methoxy-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 1970308
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1970308
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH3:17])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][C:19]([NH2:22])=[N:18]3)[C:4]=2[CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.CN[C@@H]1CCCC[C@H]1NC>CCO.O.[Cu]I>[N:23]([C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH3:17])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][C:19]([NH2:22])=[N:18]3)[C:4]=2[CH:3]=1)=[N+:24]=[N-:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 33557Sodium AzideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 59272314(R)-2'-bromo-7'-methoxy-5H-spiro[oxazole-4,9'-xanthen]-2-amineHCID 66586226sodium L-ascorbic acid

Produkt 1

HCID 86640718(S)-2'-azido-7'-methoxy-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 5 mL smith synthesizer vial was charged with (R)-2′-bromo-7′-methoxy-5H-spiro[oxazole-4,9′-xanthen]-2-amine (1.248 g, 3.46 mmol), sodium azide (0.684 g, 10.52 mmol), L-ascorbic acid sodium salt (0.057 g, 0.288 mmol), copper(I) iodide (0.131 g, 0.688 mmol), and (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (0.116 mL, 0.736 mmol) in EtOH (6.0 mL), water (2.6 mL) and the reaction was heated to 100° C. in the microwave for 35 minutes. The reaction vial was cooled to RT and concentrated on the rotary evaporator and the resulting residue was taken up in ethyl acetate (125 mL), water (50 mL) the organic layer was separated. The organic layer was dried over sodium sulfate and concentrated to yield the crude product which was purified by silica gel flash column chromatography (using a 40G ISCO silica gel cartridge), and eluted using hexanes/ethyl acetate gradient. The fractions were combined and concentrated to yield (S)-2′-azido-7′-methoxy-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a yellowish solid. MS (ESI pos. ion) m/z: 324 (M+1).

Aufarbeitung

  1. customThe reaction
  2. temperaturevial was cooled to RT
  3. concentrationconcentrated on the rotary evaporator
  4. customwater (50 mL) the organic layer was separated
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto yield the crude product which
  8. customwas purified by silica gel flash column chromatography (
  9. washeluted
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-103aa626ae2b4d49b14d6fc254007bf4
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426447B2

Notizen zur Reaktion

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