Triethylamine → tert-butyl (2RS,3RS)-2-[N-[(1RS,2RS)-2-(tert-butoxycarbonyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-5-oxotetrahydrofuran-3-carboxylate

HRID 1004326

Reaction equation

HRID 1004326 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[O:14][C:13]([CH2:15][CH:16]([CH:24]([NH:26][CH2:27]/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH3:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]([O:40][C:41]([CH:43]1[CH2:47][C:46](=[O:48])[O:45][CH:44]1[C:49](O)=[O:50])=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)(Cl)Cl.O>[C:20]([O:19][C:17]([CH:16]([CH2:15][C:13]1[O:14][C:10]([C:8](=[O:9])[NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:12]=1)[CH:24]([N:26]([CH2:27]/[CH:28]=[CH:29]/[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:49]([CH:44]1[CH:43]([C:41]([O:40][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:42])[CH2:47][C:46](=[O:48])[O:45]1)=[O:50])[CH3:25])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 18705233(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acidHCID 86755319tert-butyl (2RS,3RS)-2-{5-(phenylcarbamoyl)-2-furylmethyl}-3-{(E)-3-phenyl-2-propenylamino}butanoate

Product 1

HCID 86755318tert-butyl (2RS,3RS)-2-[N-[(1RS,2RS)-2-(tert-butoxycarbonyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-5-oxotetrahydrofuran-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

86 mg of tert-butyl (2RS,3RS)-2-{5-(phenylcarbamoyl)-2-furylmethyl}-3-{(E)-3-phenyl-2-propenylamino}butanoate prepared in Reference Example 3, 46 mg of (2RS,3RS)-3-(tert-butoxycarbonyl)-5-oxotetrahydrofuran-2-carboxylic acid prepared in Reference Example 6 and 140 μl of triethylamine were dissolved in 2 ml of chloroform and stirred with 41 mg of 2-chloro-1,3-dimethylimidazolinium chloride in 1 ml of chloroform under cooling with ice for 10 minutes and then at room temperature for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1→2/1] to give 124 mg (stoichiometric yield) of the title compound as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice for 10 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1→2/1]
  7. customto give

Sources & evidence

ORD record
ord-215f49b7da904190b070de6e10aa8cde
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Linked notes

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