1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-Fluoro-3-methyl-benzyl)-hexanoic acid (tetrahydro-pyran-2-yloxy)-amide

HRID 1158124ノート

反応式

HRID 1158124 の反応式
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]([CH2:11][CH2:12][CH2:13][CH3:14])[C:8]([OH:10])=O)=[CH:4][C:3]=1[CH3:17].[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:24][NH2:25].C1C=CC2N(O)N=NC=2C=1.C[N+]1(C)[C@H]2CC3C=CC(O)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.CCN=C=NCCCN(C)C>ClCCl.O>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:24][NH:25][C:8](=[O:10])[CH:7]([CH2:6][C:5]1[CH:15]=[CH:16][C:2]([F:1])=[C:3]([CH3:17])[CH:4]=1)[CH2:11][CH2:12][CH2:13][CH3:14]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 61063N-MethylmorphineHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 595125992-(4-Fluoro-3-methyl-benzyl)-hexanoic acid

生成物 1

HCID 595125952-(4-Fluoro-3-methyl-benzyl)-hexanoic acid (tetrahydro-pyran-2-yloxy)-amide収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(4-Fluoro-3-methyl-benzyl)-hexanoic acid (0.498 g, 2.091 mmol), O-(tetrahydro-pyran-2-yl)-hydroxylamine (0.735 g, 6.274 mmol), HOBT (0.282 g, 2.091 mmol), and N-methyl morphine (1.058 g, 10.455 mmol) in 20 mL of dichloromethane, was added EDCI (0.601 g, 3.137 mmol). After stirring at room temperature under N2 for 64 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined and dried over anhydrous Na2SO4. After removing the solvents under reduced pressure, the product was isolated by Flash chromatography (silica gel) eluting with 0-40% ethyl acetate/hexanes to give the title compound as a pale yellow solid (0.423 g, 60% yield). LC-MS: tR=9.1 min; m/z 338 (M+H)+.

後処理

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter removing the solvents under reduced pressure
  4. customthe product was isolated by Flash chromatography (silica gel)
  5. washeluting with 0-40% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-5a64fc5584e641d3af056664a5ca161b
出典データセット
uspto-grants-2010_10
特許番号
US07807720B2

反応ノート

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