Tetrahydrofuran → HCID 178504281, 화합물

HRID 470700노트

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HRID 470700 반응식
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].O1CCCC1.[NH2:18]/[C:19](=[N:36]\[OH:37])/[C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH2:22][CH2:21]1>ClCCl>[O:2]=[C:1]1[O:37][N:36]=[C:19]([C@H:20]2[CH2:21][CH2:22][C@H:23]([NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH2:24][CH2:25]2)[NH:18]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 178504282HCID 178504282, 화합물

생성물 1

HCID 178504281HCID 178504281, 화합물수율 62.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

Carbonyldiimidazole (1.24 g, 7.43 mmol) was added to a tetrahydrofuran (20 ml) solution of the compound (1.12 g, 3.71 mmol) obtained in Step 5 above under ice cooling and the resulting mixture was stirred at 50° C. for 24 hours. The reaction mixture was diluted with dichloromethane:methanol [10:1 (v/v)] and washed with 10% aqueous citric acid solution and saturated sodium bicarbonate solution in that order and then the organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→13:7→dichloromethane:methanol=49:1→19:1 (v/v)] to give 757 mg (62%) of the title compound as a colorless solid.

후처리

  1. washmethanol [10:1 (v/v)] and washed with 10% aqueous citric acid solution and saturated sodium bicarbonate solution in that order
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→13:7→dichloromethane:methanol=49:1→19:1 (v/v)]

출처 및 근거

ORD 기록
ord-34b4ef73b0774e7fb6ac1d905a658440
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629133B2

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