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

HRID 1855058ノート

反応式

HRID 1855058 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bfb622a7777453d941f2a3cb54b4c1c
出典データセット
uspto-grants-2015_02
特許番号
US08962660B2

反応ノート

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