Triethylamine → HCID 68978614、化合物

HRID 736862ノート

反応式

HRID 736862 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.[NH4+].[OH-]>O1CCCC1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:22])=[O:19])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 21685535HCID 21685535、化合物

生成物 1

HCID 68978614HCID 68978614、化合物収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid (2.13 g, 7.71 mmol) prepared in 3) was dissolved in tetrahydrofuran (32 ml) in nitrogen atmosphere, and triethylamine (1.16 ml, 8.41 mmol) and ethyl chloroformate (0.726 ml, 8.41 ml) were dropwise added under cooling with ice, followed by stirring for 30 minutes. Then, a 28% ammonia aqueous solution was dropwise added, followed by stirring for 5 minutes. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate twice. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid amide (1.60 g, 76%) as colorless solid.

後処理

  1. additionwere dropwise added
  2. temperatureunder cooling with ice
  3. stirringby stirring for 5 minutes
  4. concentrationThe reaction solution was concentrated under reduced pressure, and water
  5. additionwas added to the residue
  6. extractionfollowed by extraction with ethyl acetate twice
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-ab19e855a0bf48f5afa73da4bae4d4de
出典データセット
uspto-grants-2009_09
特許番号
US07595415B2

反応ノート

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