Diethyl Ether → tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamate

HRID 271391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271391
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3]1.[F:15][C:16]([F:29])([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17](OCC)=[O:18].CCOCC.CCCCCC>CCO>[F:15][C:16]([F:29])([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17]([NH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:3]1)=[O:18]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 14888699Ethyl 2,2-difluoro-2-(p-tolyl)acetateHCID 45091937tert-Butyl N-((1S,3S)-3-aminocyclopentyl)carbamate

Produkt 1

HCID 59834916tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of tert-butyl [(1S,3S)-3-aminocyclopentyl]carbamate (1.36 g, 6.8 mmol) and ethyl difluoro(4-methylphenyl)acetate (1.45 g, 6.8 mmol) in EtOH (5 mL) was stirred at reflux for 16 h. The solution was cooled to rt. whereupon it solidified. Et2O (6 mL) and hexane (3 mL) were added and the mixture was stirred for 3 h and the solids collected by filtration, rinsing with Et2O (2 mL), and dried to give the title compound (1.051 g) as a solid; MS=313.4 (M+1-isobutylene).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. filtrationthe solids collected by filtration
  3. washrinsing with Et2O (2 mL)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e8e34dd190884ddc986aaa8d68156ca6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452893B2

Notizen zur Reaktion

Wird geladen…