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Triethylamine → (1-{[4-(-Ethoxymethyl-1h-imidazol-2-yl)-1-isopropyl-3-methyl-4-oxo-but-2-enyl]-methyl-carbonyl}-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester

HRID 133831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 133831
C(OC(=O)N([CH:9]([CH:24]([CH3:26])[CH3:25])[CH:10]=[C:11]([CH3:23])[C:12]([C:14]1[N:15]([CH2:19][O:20][CH2:21][CH3:22])[CH:16]=[CH:17][N:18]=1)=[O:13])C)(C)(C)C.[C:28]([O:32][C:33]([NH:35][CH:36]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:37]([OH:39])=O)=[O:34])([CH3:31])([CH3:30])[CH3:29].[CH2:44](OP(ON1C(=O)C2C=CC=CC=2N=N1)(OCC)=O)C.C(N(CC)CC)C>Cl.O1CCOCC1.ClCCl.ClCCl.O>[C:28]([O:32][C:33](=[O:34])[NH:35][CH:36]([C:37]([CH2:44][CH:9]([CH:24]([CH3:25])[CH3:26])[CH:10]=[C:11]([CH3:23])[C:12]([C:14]1[N:15]([CH2:19][O:20][CH2:21][CH3:22])[CH:16]=[CH:17][N:18]=1)=[O:13])=[O:39])[C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:29])([CH3:30])[CH3:31]
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Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 69017807[4-(1-Ethoxymethyl-1h-imidazol-2-yl)-1-isopropyl-3-methyl-4-oxo-but-2-enyl]-methyl-carbamic acid tert-butyl ester

Produkt 1

HCID 69020063
(1-{[4-(-Ethoxymethyl-1h-imidazol-2-yl)-1-isopropyl-3-methyl-4-oxo-but-2-enyl]-methyl-carbonyl}-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 204431481,4-Dioxane hydrochlorideLösungsmittelHCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

[4-(1-Ethoxymethyl-1H-imidazol-2-yl)-1-isopropyl-3-methyl-4-oxo-but-2-enyl]-methyl-carbamic acid tert-butyl ester (496 mg, 1.31 mmole) is stirred in 4N hydrochloric acid/dioxane at room temperature under nitrogen for 2 hours. The solvent is removed in vacuo. Dichloromethane is added to the residue and evaporated (this step is repeated twice) to give a white solid amino intermediate which then stirred with 2-tert-Butoxycarbonylamino-3,3-dimethyl-butyric acid (410.5 mg, 1.78 mmole), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT, 531 mg, 1.77 mmole) and triethylamine (0.49 ml, 3.55 mmole) in 4 ml dichloromethane at room temperature overnight. The reaction mixture is diluted with dichloromethane/water. Organic layer is separated. The aqueous layer is extracted twice with dichloromethane. The combined organic extracted are washed with citric acid (4 ml), sodium carbonate (6 ml) and brine, dried over sodium sulfate, filtered, concentrated in vacuo. The residue is flash chromatographed with hexane/ethyl acetate from 5:1 to 1:1 to give a white crystals, (1-{[4-(-Ethoxymethyl-1H-imidazol-2-yl)-1-isopropyl-3-methyl-4-oxo-but-2-enyl]-methyl-carbonyl}-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester: 171 mg (26%). MS(ES+): (M+H)=493.2

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. additionDichloromethane is added to the residue
  3. customevaporated (this step
  4. customto give a white solid amino intermediate which
  5. customOrganic layer is separated
  6. extractionThe aqueous layer is extracted twice with dichloromethane
  7. extractionThe combined organic extracted
  8. washare washed with citric acid (4 ml), sodium carbonate (6 ml) and brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customchromatographed with hexane/ethyl acetate from 5:1 to 1:1

Quellen und Nachweise

ORD-Eintrag
ord-8e64dcc6990b40be99c8d84eb4c6fd47
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07390910B2

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