1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 3-[(2-dimethylaminoethyl)carbamoylmethoxy]-5-hydroxybenzoate

HRID 1740317ノート

反応式

HRID 1740317 の反応式
[C:1]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])([OH:3])=O.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][C:1]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([OH:16])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:3]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 11253108Methyl 3-carboxymethoxy-5-hydroxybenzoate

生成物 1

HCID 21838125Methyl 3-[(2-dimethylaminoethyl)carbamoylmethoxy]-5-hydroxybenzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of methyl 3-carboxymethoxy-5-hydroxybenzoate (2 g), N,N-dimethylethylenediamine (1.07 ml) and 1-hydroxybenzotriazole (1.31 g) in N,N-dimethylformamide (40 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.86 g) under ice cooling. After stirring at room temperature for 5 hours, the solvent of the reaction mixture was removed under reduced pressure. The residue was purified by column chromatography on aluminum eluting with a mixture of chloroform and methanol (20:1 to 5:1). The fractions containing the desired product were collected and evaporated in vacuo. Then the residue was triturated with diethyl ether, collected by filtration and washed with diethyl ether to give methyl 3-[(2-dimethylaminoethyl)carbamoylmethoxy]-5-hydroxybenzoate (1.94 g).

後処理

  1. customthe solvent of the reaction mixture was removed under reduced pressure
  2. customThe residue was purified by column chromatography on aluminum eluting with a mixture of chloroform and methanol (20:1 to 5:1)
  3. additionThe fractions containing the desired product
  4. customwere collected
  5. customevaporated in vacuo
  6. customThen the residue was triturated with diethyl ether
  7. filtrationcollected by filtration
  8. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-c6824011d78f4ce6929d5238ce7acd3a
出典データセット
uspto-grants-1999_10
特許番号
US05968985

反応ノート

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