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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
Notes
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Reaction equation

HRID 133831 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 204431481,4-Dioxane hydrochlorideSolventHCID 21908982Water methylene chlorideSolvent

Procedure

[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

Workup

  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

Sources & evidence

ORD record
ord-8e64dcc6990b40be99c8d84eb4c6fd47
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07390910B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes