1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-((3S)-6-((2,4-Dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)-2-hydroxy-3-methylbutanamide

HRID 591529ノート

反応式

HRID 591529 の反応式
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][NH2:15])[CH2:11][O:12][C:8]=2[CH:7]=1.[OH:23][CH:24]([CH:28]([CH3:30])[CH3:29])[C:25](O)=[O:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][NH:15][C:25](=[O:26])[CH:24]([OH:23])[CH:28]([CH3:30])[CH3:29])[CH2:11][O:12][C:8]=2[CH:7]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 99823(+-)-2-Hydroxyisovaleric acidHCID 516892Sodium BicarbonateHCID 897679342-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanamine

生成物 1

HCID 118656156N-(2-((3S)-6-((2,4-Dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)-2-hydroxy-3-methylbutanamide収率 59.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanamine (33.8 mg) and DMF (dry) (5 mL) were added 2-hydroxy-3-methylbutanoic acid (17.72 mg), EDCI (31.0 mg) and HOBt (27.0 mg). The mixture was stirred at room temperature overnight. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (26.0 mg).

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-000be4ddf2bc457da56663ff6f5921ea
出典データセット
uspto-grants-2016_01
特許番号
US09238639B2

反応ノート

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