1-Hydroxybenzotriazole → (4R)-4-(4-fluoro-3-methylphenyl)-4-methoxy-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

HRID 1643265ノート

反応式

HRID 1643265 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH2:8].C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+].[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:37][CH3:38])[CH2:32][CH2:33][C:34](O)=[O:35])=[CH:27][C:26]=1[CH3:39].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:37][CH3:38])[CH2:32][CH2:33][C:34]([NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[O:35])=[CH:27][C:26]=1[CH3:39]

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 59568829(R)-4-(4-Fluoro-3-methylphenyl)-4-methoxybutanoic acid

生成物 1

HCID 86647280(4R)-4-(4-fluoro-3-methylphenyl)-4-methoxy-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a mixture of O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (175 mg, 1.5 mmol), HOBt (810 mg, 6.0 mmol), NaHCO3 (1.0 g, 11.9 mmol) and the crude (R)-4-(4-fluoro-3-methylphenyl)-4-methoxybutanoic acid in 60 mL CH2Cl2 was added EDC.HCl (958 mg, 5.0 mmol). The mixture was stirred for 3 h at 25° C. The solvent was removed under reduced pressure and the product isolated by flash column chromatography, eluting with 10% to 60% Ethyl acetate/Hexane gradient solvent to give 208 mg of the title compound.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe product isolated by flash column chromatography
  3. washeluting with 10% to 60% Ethyl acetate/Hexane gradient solvent

出典と根拠

ORDレコード
ord-2081bd4068574f2c91fef1ab69070180
出典データセット
uspto-grants-2012_02
特許番号
US08119692B2

反応ノート

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