Ethyl chloroformate → 2-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetyl azide

HRID 1855058노트

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HRID 1855058 반응식
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][C:23]([OH:25])=O)([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC)=O.[N-:32]=[N+:33]=[N-:34].[Na+]>CC(C)=O.O>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][C:23]([N:32]=[N+:33]=[N-:34])=[O:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 904093542-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid

생성물 1

HCID 904082032-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetyl azide수율 100%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid (6A: 97 mg, 0.287 mmol) in acetone (1 mL) at 0° C. was added TEA (0.064 mL, 0.459 mmol), followed by ethyl chloroformate (0.044 mL, 0.459 mmol) dropwise. The mixture was stirred at 0° C. for 30 min. A solution of NaN3 (37.3 mg, 0.573 mmol) in 0.5 mL water was added slowly and the mixture was stirred at 0° C. for another 1 h. The reaction mixture was then poured into ice-water (5 mL) and extracted with diethyl ether (3×2 mL). The combined extracts were washed successively with water (5 mL), saturated aqueous NaHCO3 (5 mL) and water (5 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound (104 mg, 100% yield). LCMS, [M+Na]+=386.1.

후처리

  1. stirringthe mixture was stirred at 0° C. for another 1 h
  2. extractionextracted with diethyl ether (3×2 mL)
  3. washThe combined extracts were washed successively with water (5 mL), saturated aqueous NaHCO3 (5 mL) and water (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8bfb622a7777453d941f2a3cb54b4c1c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962660B2

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