Ammonium Chloride → (S)-2-(4-isobutyl-phenyl)-propionic acid 2-(3,5-dichloro-pyridin-4-yl)-1-(3,4-dimethoxy-phenyl)-ethyl ester

HRID 220715

反応式

HRID 220715 の反応式
Cl.C(N=C=NCCCN(C)C)C.[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([Cl:33])[C:19]=1[CH2:20][CH:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1)[OH:22].[CH2:34]([C:38]1[CH:43]=[CH:42][C:41]([C@H:44]([CH3:48])[C:45](O)=[O:46])=[CH:40][CH:39]=1)[CH:35]([CH3:37])[CH3:36].[NH4+].[Cl-]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:33][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:13])[C:19]=1[CH2:20][CH:21]([O:22][C:45](=[O:46])[C@H:44]([C:41]1[CH:42]=[CH:43][C:38]([CH2:34][CH:35]([CH3:37])[CH3:36])=[CH:39][CH:40]=1)[CH3:48])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 39912DexibuprofenHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 670959732-(3,5-Dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethanol

生成物 1

HCID 67096033(S)-2-(4-isobutyl-phenyl)-propionic acid 2-(3,5-dichloro-pyridin-4-yl)-1-(3,4-dimethoxy-phenyl)-ethyl ester収率 82.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

(1-Ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride) (EDC.HCl) (345 mg, 3 eq.) is added to a solution of 2-(3,5-dichloro-pyridin-4-yl)-1-(3,4-dimethoxy-phenyl)-ethanol (200 mg, 1 eq.), (S)-2-(4-isobutyl-phenyl)-propionic acid (148 mg, 1.2 eq.) and 4-dimethylaminopyridine (DMAP) (37 mg, 0.5 eq.) in dry CH2Cl2 (8 mL) at room temperature under nitrogen atmosphere. The mixture is stirred at room temperature overnight, then it is treated with a saturated solution of NH4Cl (20 ml) and extracted with EtOAc (2×20 ml). The combined organic layer are dried over Na2SO4 and the solvent is evaporated. The crude is purified by flash chromatography on silica gel in gradient elution (from petroleum ether/EtOAc 9/1 v/v to petroleum ether/EtOAc 7/3 v/v) to yield 259 mg of pure compound.

後処理

  1. extractionextracted with EtOAc (2×20 ml)
  2. dry with materialThe combined organic layer are dried over Na2SO4
  3. customthe solvent is evaporated
  4. customThe crude is purified by flash chromatography on silica gel in gradient elution (from petroleum ether/EtOAc 9/1 v/v to petroleum ether/EtOAc 7/3 v/v)

出典と根拠

ORDレコード
ord-fe0af1d35e0d44a29c487f37c1987e1a
出典データセット
uspto-grants-2012_06
特許番号
US08203000B2

関連ノート

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