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Ethyl chloroformate → Benzamide, 4-(acetylamino)-5-chloro-N-[(2-ethyloctahydrocyclopenta[c]pyrrol-1-yl)methyl]-2-methoxy-

HRID 1833407
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1833407
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[C:9]([Cl:16])=[CH:8][C:4]=1[C:5]([OH:7])=O.ClC(OCC)=O.[CH2:23]([N:25]1[CH2:32][CH:31]2[CH:27]([CH2:28][CH2:29][CH2:30]2)[CH:26]1[CH2:33][NH2:34])[CH3:24]>O1CCCC1.C(N(CC)CC)C>[CH2:23]([N:25]1[CH2:32][CH:31]2[CH:27]([CH2:28][CH2:29][CH2:30]2)[CH:26]1[CH2:33][NH:34][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:16])[C:10]([NH:12][C:13](=[O:15])[CH3:14])=[CH:11][C:3]=1[O:2][CH3:1])[CH3:24]
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Komponenten

6

Edukt 3

HCID 10928Ethyl chloroformateHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 85848305HCID 85848305, Verbindung

Produkt 1

HCID 86733791Benzamide, 4-(acetylamino)-5-chloro-N-[(2-ethyloctahydrocyclopenta[c]pyrrol-1-yl)methyl]-2-methoxy-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
2×
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 6 parts of 2-methoxy-4-acetylamino-5-chloro benzoic acid in 50 parts of anhydrous tetrahydrofuran, were added 2.5 parts of triethylamine. The solution thus obtained was poured portionwise in a mixture of 2.7 parts of ethyl chloroformate in 80 parts of tetrahydrofuran maintained at 0° C. After stirring for 10 minutes, 4.1. parts of N-ethyl-2-aminomethyl-3-azabicyclo (3,3,0) octane were added. After being maintained at room temperature for 10 minutes, the temperature was progressively increased and, finally, the reaction mixture was refluxed for 60 minutes. After cooling, the mixture was filtered and the filtrate was evaporated in vacuo. After recrystallization in 50 parts of ethyl acetate, there were obtained 5.5 parts of N-ethyl-2-(2-methoxy-4-acetylamino-5-chloro benzamido methyl)-3-azabicyclo (3,3,0) octane, M.P. 156°-157° C (ethyl acetate).

Aufarbeitung

  1. customThe solution thus obtained
  2. temperatureAfter being maintained at room temperature for 10 minutes
  3. temperaturethe temperature was progressively increased
  4. temperaturefinally, the reaction mixture was refluxed for 60 minutes
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered
  7. customthe filtrate was evaporated in vacuo
  8. customAfter recrystallization in 50 parts of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cfafa8d9228a466abce7c71a51184e64
Quelldatensatz
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04066662

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