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Propionyl chloride → Ammonia

HRID 1839221
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1839221
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([CH2:18][NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>C(Cl)Cl>[NH3:11].[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([CH2:18][N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26](=[O:29])[CH2:27][CH3:28])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 62324Propionyl chlorideHCID 205980843-Phenylaminomethyl-azepane-1-carboxylic acid benzyl ester

Produkt 2

HCID 222AmmoniaHCID 205980873-[(Phenyl-propionyl-amino)-methyl]-azepane-1-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Et(iPr)2N (0.24 mL, 1.38 mmol) was added to a stirring solution of crude 3-phenylaminomethyl-azepane-1-carboxylic acid benzyl ester (148) in CH2Cl2 (2.3 mL) under N2. The reaction was cooled to 0° C. in an ice bath, then propionyl chloride (0.22 mL, 2.53 mmol) was added dropwise. The reaction was allowed to warm to room temperature overnight. The reaction was then judged complete by TLC. It was concentrated in vacuo and EtOAc and 10% NaOH (aq) were added. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo, and purified by automated silica gel chromatography with 96:2:2 Hexanes:CH2Cl2:2N NH3 in EtOH to obtain 3-[(phenyl-propionyl-amino)-methyl]-azepane-1-carboxylic acid benzyl ester (149) (0.3266 g) in 72% yield for two steps.

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. concentrationIt was concentrated in vacuo and EtOAc and 10% NaOH (aq)
  3. additionwere added
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by automated silica gel chromatography with 96:2:2 Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4cf64fad1007427c93b47e767f8a6a53
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06677332B1

Notizen zur Reaktion

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