1,1'-Carbonyldiimidazole → N-(2,6-dichlorobenzoyl)-4-[2-[N-(methanesulfonyl)carbamoyl]phenyl]-L-phenylalanine methyl ester

HRID 1060423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060423
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29](O)=[O:30])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47].C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29](=[O:30])[NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Komponenten

7

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53640164N-(2,6-dichlorobenzoyl)-4-(2-carboxyphenyl)-L-phenylalanine methyl ester

Produkt 1

HCID 53805245N-(2,6-dichlorobenzoyl)-4-[2-[N-(methanesulfonyl)carbamoyl]phenyl]-L-phenylalanine methyl esterAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(2,6-Dichlorobenzoyl)-4-(2-carboxyphenyl)-L-phenylalanine methyl ester (57.0 mg) was dissolved in anhydrous THF (1 mL), carbonyldiimidazole (23.5 mg) was added and the mixture was stirred at room temperature under N2 for 2 h. Methanesulfonamide (17.2 mg) and DBU (27 μL) were added and the mixture was stirred for an additional 18 h. The mixture was then heated to 40° C., stirred for 7 h at the same temperature, cooled to room temperature, diluted with EtOAc, washed with 1N HCl and then brine, dried (MgSO4) and evaporated. The residue was purified by preparative TLC (silica gel) using CH2Cl2/MeOH (100:1 to 10:1) as an eluent to give N-(2,6-dichlorobenzoyl)-4-[2-[N-(methanesulfonyl)carbamoyl]phenyl]-L-phenylalanine methyl ester (37.0 mg). ESMS: m/z 549 (MH+).

Aufarbeitung

  1. stirringthe mixture was stirred for an additional 18 h
  2. temperatureThe mixture was then heated to 40° C.
  3. stirringstirred for 7 h at the same temperature
  4. temperaturecooled to room temperature
  5. washwashed with 1N HCl
  6. dry with materialbrine, dried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by preparative TLC (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-60a6097349d54aa588c5481023a698cb
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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