1-Hydroxybenzotriazole → HCID 68414528, Verbindung

HRID 220313

Reaktionsgleichung

Reaktionsgleichung von HRID 220313
C1([C:7]2[N:8]=[C:9]([CH2:26][CH2:27][C:28]([OH:30])=O)[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)C=CC=CC=1.CCN(C(C)C)C(C)C.[CH:40]1[CH:41]=[CH:42][C:43]2N(O)N=N[C:44]=2[CH:45]=1.[CH3:50][NH:51][CH2:52][CH2:53][C:54]1([OH:68])[CH2:59][CH:58]2[CH2:60][CH2:61][CH:55]1[CH:56]=[C:57]2[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>C1COCC1.C(Cl)Cl.C(Cl)CCl>[C:44]1([C:7]2[N:8]=[C:9]([CH2:26][CH2:27][C:28]([N:51]([CH2:52][CH2:53][C@:54]3([OH:68])[CH2:59][C@H:58]4[CH2:60][CH2:61][C@@H:55]3[CH:56]=[C:57]4[C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)[CH3:50])=[O:30])[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:23])[CH3:24])[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:45]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 684143723-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acidHCID 68415512rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Produkt 1

HCID 68414528HCID 68414528, VerbindungAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

145 mg of 3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid were dissolved in THF (0.13 mL)/DCM (0.5 mL). 0.160 mL of DIPEA, 50 mg of HOBt and 71 mg of EDC were added sequentially at rt. The reaction mixture was stirred for 5 min then 80 mg of rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol were added at rt. The reaction mixture was stirred on at rt then diluted with DCM and washed with sat.-NaHCO3 and brine. The organic phase was dried over anh. Na2SO4, filtered and concentrated in vacuo. The resulting crude material was purified by CC using EtOAc/MeOH/NEt3 as eluant from 100/0/1 to 95/5/1 to yield 189 mg of rac-3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-N-[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-N-methyl-propionamide as a yellow oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred on at rt
  2. washwashed with sat.-NaHCO3 and brine
  3. dry with materialThe organic phase was dried over anh. Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude material was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-0dae70123d2048afbcb8e128730f1905
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202885B2

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