1,1'-Carbonyldiimidazole → tert-butyl (3S,5R)-3-{[(benzyloxy)carbonyl]amino}-5-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate

HRID 2192829노트

반응식

HRID 2192829 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][C@H:14](C(O)=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:40]([O:42][C:43](=[O:48])[CH2:44][C:45]([K])=[O:46])[CH3:41].[Cl-].[Mg+2].[Cl-]>C1COCC1.Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:13][C@@H:14]([C:45](=[O:46])[CH2:44][C:43]([O:42][CH2:40][CH3:41])=[O:48])[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:17]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 5360315Magnesium ChlorideHCID 59356597(3R,5S)-5-(benzyloxycarbonylamino)-1-tert-butoxycarbonyl-piperidine-3-carboxylic acidHCID 178472227HCID 178472227, 화합물

생성물 1

HCID 59625444tert-butyl (3S,5R)-3-{[(benzyloxy)carbonyl]amino}-5-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate수율 17.2%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (3R,5S)-5-{[(benzyloxy)carbonyl]amino}-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (2.25 g) in THF (60 ml) was added 1,1′-carbonylbis(1H-imidazole) (1.20 g) and the mixture was stirred at room temperature for 2 hr. (3-Ethoxy-3-oxopropanoyl)potassium (1.26 g) and magnesium chloride (700 mg) were added and the reaction mixture was stirred with heating to reflux for 4 hr. After cooling to room temperature, the reaction mixture was diluted with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed successively with 3.5 M aqueous potassium carbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (10:90-80:20) and concentrated under reduced pressure to give the object compound (460 mg).

후처리

  1. stirringthe reaction mixture was stirred
  2. temperaturewith heating
  3. temperatureto reflux for 4 hr
  4. temperatureAfter cooling to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed successively with 3.5 M aqueous potassium carbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. washeluted with ethyl acetate-hexane (10:90-80:20)
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b6b1608d561e4ce399452ac549f1fe16
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329691B2

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