1,2-Dichloroethane → 4-(3-(Tert-butoxycarbonylamino)-1-(4-carbamoyl-3-fluorophenylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate

HRID 1020140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020140
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[CH:12]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=2)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][C:5]=1[F:31])(=[O:3])[NH2:2].C(Cl)CCl.[CH3:36][C:37]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:38]=1[C:39](O)=[O:40]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:36][C:37]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:38]=1[C:39]([O:29][CH2:28][C:25]1[CH:24]=[CH:23][C:22]([CH:12]([CH2:13][NH:14][C:15]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:21])[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[NH2:2])=[C:5]([F:31])[CH:6]=2)=[O:30])=[CH:27][CH:26]=1)=[O:40]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 118972,4-Dimethylbenzoic acidHCID 59563726Tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate

Produkt 1

HCID 595636994-(3-(Tert-butoxycarbonylamino)-1-(4-carbamoyl-3-fluorophenylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To tert-butyl 3-(4-carbamoyl-3-fluorophenylamino)-2-(4-(hydroxymethyl)phenyl)-3-oxopropylcarbamate (E337-1) in pyridine was added was added EDC, DMAP, and 2,4-dimethylbenzoic acid, and the solution was stirred overnight at room temperature. The mixture was poured into NaHCO3(sat) and extracted with EtOAc. The organics were dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-5% MeOH/CH2Cl2 gradient) gave pure 4-(3-(tert-butoxycarbonylamino)-1-(4-carbamoyl-3-fluorophenylamino)-1-oxopropan-2-yl)benzyl 2,4-dimethylbenzoate (E337-2).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2155690a60414d72bbac36ca639ed422
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716310B2

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