Diisopropylethylamine → (5R)-3-(3-Fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 1371823노트

반응식

HRID 1371823 반응식
C(N(CC)C(C)C)(C)C.[NH2:10][CH2:11][C@@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH2:13]1.Cl[CH:26](Cl)[C:27](=[N:29][NH:30]S(C1C=CC(C)=CC=1)(=O)=O)[CH3:28]>CO>[F:24][C:20]1[CH:19]=[C:18]([N:14]2[CH2:13][C@H:12]([CH2:11][N:10]3[CH:26]=[C:27]([CH3:28])[N:29]=[N:30]3)[O:16][C:15]2=[O:17])[CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 11401559(5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-oneHCID 73181071N'-[2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide

생성물 1

HCID 58778317(5R)-3-(3-Fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one수율 72%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

N,N-Diisopropylethylamine (3.20 ml, 18.35 mmol) was added to a solution of (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one (0.77 g, 3.57 mmol) (see Patent Application: Dong Pharmaceuticals WO 01/94342) in anhydrous methanol (25 ml). The solution was cooled to 0° C., and N′-[2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide (1.28 g, 4.58 mmol) was added. The solution was warmed to room temperature and stirred overnight. The reaction mixture was then concentrated under vacuum and chromatographed on silica gel using 2% methanol/dichloromethane to give 0.71 g of the title product.

후처리

  1. temperatureThe solution was warmed to room temperature
  2. concentrationThe reaction mixture was then concentrated under vacuum
  3. customchromatographed on silica gel using 2% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-a66e0f5d024a4afbb2a2cbffc7dac4a5
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157482B2

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