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Ammonia → tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamate

HRID 1828412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1828412
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.N>O1CCCC1>[NH2:22][C:17](=[O:19])[CH2:16][CH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 220637293-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl)propanoic acid

Produkt 1

HCID 22063511tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamateAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

3-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl}propanoic acid (11.16 g, 41.92 mmol) dissolved in tetrahydrofuran (200 ml) was added with triethylamine (9 ml, 62.89 mmol), cooled with ice, and then added dropwise with ethyl chloroformate (6 ml, 62.89 mmol). The reaction mixture was stirred for 10 minutes, and then added with aqueous ammonia (50 ml) dissolved in tetrahydrofuran (50 ml) at 0° C. The reaction mixture was stirred for 20 minutes under ice cooling, and then the solvent was evaporated under reduced pressure. The resulting residue was washed with water and extracted with chloroform. The resulting organic layer was washed with saturated brine, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 11.794 g (100%) of the title compound as brown crystals without purification.

Aufarbeitung

  1. temperaturecooled with ice
  2. stirringThe reaction mixture was stirred for 20 minutes under ice cooling
  3. customthe solvent was evaporated under reduced pressure
  4. washThe resulting residue was washed with water
  5. extractionextracted with chloroform
  6. washThe resulting organic layer was washed with saturated brine
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6d35462f82eb462697301e392a270694
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07056917B2

Notizen zur Reaktion

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