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

HRID 747228노트

반응식

HRID 747228 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 70.2%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

N,N-Diisopropylethylamine (3.20 mL, 18.35 mM) was added to a solution of (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one (0.77 g, 3.57 mM; see Dong Pharmaceuticals WO 0194342) 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 mM) 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-06845fd9ba70447abe3ec36d64e84578
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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