Water → Benzyl 4-(2-(4-propyl-1H-1,2,3-triazol-1-yl)acetyl)morpholine-2-carboxylate

HRID 253146

Reaktionsgleichung

Reaktionsgleichung von HRID 253146
[N:1]([CH2:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=[O:6])=[N+:2]=[N-:3].O.O=[C:25]1O[C@H:30]([C@H:32](CO)O)[C:28]([O-])=[C:26]1O.[Na+].C#CCCC>CC(O)(C)C.CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:28]([C:26]1[N:3]=[N:2][N:1]([CH2:4][C:5]([N:7]2[CH2:12][CH2:11][O:10][CH:9]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:8]2)=[O:6])[CH:25]=1)[CH2:30][CH3:32]

Komponenten

8

Edukt 4

HCID 962WaterHCID 123091-PentyneHCID 23667548Sodium AscorbateHCID 86614022Benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate

Produkt 1

HCID 66845266Benzyl 4-(2-(4-propyl-1H-1,2,3-triazol-1-yl)acetyl)morpholine-2-carboxylateAusbeute 875 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a sealable vessel, benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate (0.096 g, 0.32 mmol) was suspended in t-BuOH (1 mL) and water (1 mL) was added. An aqueous solution of sodium ascorbate (1.0 M, 0.032 ml, 0.032 mmol) and an aqueous solution of copper(II) sulfate pentahydrate (0.30 M, 0.079 ml, 0.024 mmol) were added, followed by pent-1-yne (0.040 ml, 0.41 mmol). The vessel was sealed and placed in a 65 deg oil bath, whereupon the mixture was stirred for 14 h. The reaction mixture was cooled to RT, taken up in EtOAc (60 mL), and the organic layer was extracted with dilute sodium bicarbonate (5 mL), dilute brine (5 mL), and saturated brine (5 mL), then was dried over sodium sulfate and concentrated. The residue was purified through silica gel (25 mL) eluting with EtOAc, affording the title compound (105 mg, 0.28 mmol). MS m/z 373 (M+1).

Aufarbeitung

  1. customThe vessel was sealed
  2. customplaced in a 65 deg
  3. extractionthe organic layer was extracted with dilute sodium bicarbonate (5 mL), dilute brine (5 mL), and saturated brine (5 mL)
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified through silica gel (25 mL)
  7. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-faeb4f8a57de4cb992633bfb8d63a567
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872009B2

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