Dicyclohexylcarbodiimide → 2-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide

HRID 455542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455542
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([NH2:17])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([NH:25][C@H:26]([C:31](O)=[O:32])[C@H:27]([CH2:29][CH3:30])[CH3:28])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[C:18]([NH:25][CH:26]([CH:27]([CH3:28])[CH2:29][CH3:30])[C:31]([NH:17][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:32])([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19]

Komponenten

5

Edukt 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 134772DidesmethylsibutramineHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Produkt 1

HCID 673857212-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

250 mg of 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (II) and 210 mg of Boc-isoleucine (R in Formula is Boc) was dissolved in anhydrous THF (5 mL). 220 mg DCC was dissolved in 25 mL anhydrous THF. The solution of DCC in THF was added dropwisely into the reaction solution, and then stirred overnight at room temperature to give white precipitate. The solid was filtered off and washed for at least three times with anhydrous ethyl ether. The filtrate and washed ethyl ether were collected, evaporated and purified by column chromatography to give title compound 2-(Boc-amino)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide (Formula I, wherein R is Boc).

Aufarbeitung

  1. customto give white precipitate
  2. filtrationThe solid was filtered off
  3. washwashed for at least three times with anhydrous ethyl ether
  4. washThe filtrate and washed ethyl ether
  5. customwere collected
  6. customevaporated
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d065b5ae9cbd43f6adfce258ba1c4684
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497305B2

Notizen zur Reaktion

Wird geladen…