1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid tert-butoxy-amide

HRID 885502ノート

反応式

HRID 885502 の反応式
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[C:11]([OH:13])=O)=[CH:4][C:3]=1[CH3:18].[C:19]([O:23][NH2:24])([CH3:22])([CH3:21])[CH3:20].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>[C:19]([O:23][NH:24][C:11](=[O:13])[C@H:10]([NH:9][C:5]1[CH:4]=[C:3]([CH3:18])[C:2]([F:1])=[C:7]([CH3:8])[CH:6]=1)[CH2:14][CH2:15][CH2:16][CH3:17])([CH3:22])([CH3:21])[CH3:20]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 61063N-MethylmorphineHCID 757711-HydroxybenzotriazoleHCID 2777907O-tert-butylhydroxylamineHCID 69189506(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid

生成物 1

HCID 86667068(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-hexanoic acid tert-butoxy-amide収率 38.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of crude (R)-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid (ca. 6.0 mmol), O-tert-butyl-hydroxyamine (2.261 g, 18.0 mmol), HOBT (0.811 g, 6.0 mmol), and N-methyl morphine (3.036 g, 30.0 mmol) in 20 mL of dichloromethane, was added EDCI (1.725 g, 9.0 mmol). After stirring at room temperature under N2 for 44 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 and the solvents removed under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as a pale yellow semi-solid (0.747 g, 38% yield). LC-MS: tR=8.8 min; m/z 325 (M+H)+.

後処理

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customthe solvents removed under reduced pressure
  4. customThe product was isolated by Flash chromatography (silica gel)
  5. washeluting with 0-30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-1ff177eb7e8149a3a056da007a31c06c
出典データセット
uspto-grants-2012_08
特許番号
US08242174B2

反応ノート

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