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

반응식

HRID 1004326 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-215f49b7da904190b070de6e10aa8cde
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048894

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