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 591529노트

반응식

HRID 591529 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-000be4ddf2bc457da56663ff6f5921ea
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238639B2

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