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

반응식

HRID 220715 반응식
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

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 39912DexibuprofenHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 670959732-(3,5-Dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethanol

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe0af1d35e0d44a29c487f37c1987e1a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08203000B2

연결된 노트

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