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Cyclopentanecarbonyl chloride → ethyl (RS)-(4-cyano-phenylamino)-[3-(cyclopentanecarbonyl-amino)-5-ethyl-phenyl]-acetate

HRID 1066622
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1066622
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:18]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=1.C(N(C(C)C)CC)(C)C.OS([O-])(=O)=O.[K+]>C(Cl)Cl>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([NH:24][CH:18]([C:12]2[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=[C:10]([NH:9][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:11]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:26][CH:27]=1)#[N:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 86583558ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate

Produkt 1

HCID 86583560ethyl (RS)-(4-cyano-phenylamino)-[3-(cyclopentanecarbonyl-amino)-5-ethyl-phenyl]-acetateAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Cyclopentanecarbonyl chloride (0.104 ml, 0.85 mmol) was added dropwise at 0° C. to a solution of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (250 mg, 0.772 mmol) obtained in Example 223.4 and diisopropylethylamine (0.146 ml, 0.85 mmol) in CH2Cl2 (5 ml). The reaction mixture was warmed slowly (2 h.) to room temperature. A saturated aqueous solution of KHSO4 was added and the mixture was extracted with EtOAc. The organic phase was washed with H2O, dried and filtered, and the filtrate was concentrated. The residue was purified by chromatography (SiO2, hexane→hexane/EtOAc 2:1). There were obtained 215 mg (66%) of ethyl (RS)-(4-cyano-phenylamino)-[3-(cyclopentanecarbonyl-amino)-5-ethyl-phenyl]-acetate as a colorless foam; MS: 418 ([M−H]−).

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with H2O
  3. customdried
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (SiO2, hexane→hexane/EtOAc 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6cc5b9f7c33e4eea8399a041af6d52c1
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06242644B1

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