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

HRID 1740317노트

반응식

HRID 1740317 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6824011d78f4ce6929d5238ce7acd3a
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968985

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