Triethylamine → N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide

HRID 1886741

反応式

HRID 1886741 の反応式
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].[OH:8]N1C(=O)CCC1=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23](O)[CH3:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[OH:8][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 857534-Amino-alpha-methylbenzenemethanolHCID 86640145N-hydroxysuccinimide-(4-pentynoate)

生成物 1

HCID 58427477N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

N-hydroxysuccinimide-(4-pentynoate) (Ref: Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V., Structurally Diverse Dendritic Libraries: A Highly Efficient Functionalization Approach Using Click Chemistry. Macromolecules 2005, 38, (9), 3663-3678.) (200 mg, 1.0 mmol) and p-aminophenylethanol (125 mg, 0.9 mmol) were dissolved in 2 mL of dichloromethane together with triethyl amine (140 μL, 1.0 mmol), and 5 drops of dimethyl formamide. The reaction mixture was stirred at room temperature for 2 hours. The crude reaction product was concentrated, dissolved in 10 mL of ethyl acetate and washed with 5 mL of water followed by, 5 mL of 0.5 M HCl (aq.), 5 mL of 10 NaHCO3 (aq.) and finally 5 mL of water. The organic phase was dried with MgSO4, filtered, and the solvent was evaporated. The product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E). The product N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide was characterized by NMR and MALDI-TOF.

後処理

  1. customThe crude reaction product
  2. concentrationwas concentrated
  3. dissolutiondissolved in 10 mL of ethyl acetate
  4. washwashed with 5 mL of water
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E)

出典と根拠

ORDレコード
ord-51dba3c42d9742caa5f52dc5cdc9f010
出典データセット
uspto-grants-2013_08
特許番号
US08501212B2

関連ノート

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