Tetrahydrofuran → (4R,5S)-4-Methyl-3-((R)-4-methyl-heptanoyl)-5-phenyl-oxazolidin-2-one

HRID 479041노트

반응식

HRID 479041 반응식
[CH3:1][C@H:2]([CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][C:5]([OH:7])=O.C(N(CC)CC)C.[CH3:18][C:19]([CH3:24])(C)[C:20](Cl)=[O:21].[Li+].[Cl-].[O:27]1[CH2:31][CH2:30][NH:29][C:28]1=O.[CH2:33]1[CH2:37]OC[CH2:34]1>>[CH3:31][C@@H:30]1[C@H:20]([C:19]2[CH:24]=[CH:37][CH:33]=[CH:34][CH:18]=2)[O:21][C:28](=[O:27])[N:29]1[C:5](=[O:7])[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:8][CH2:9][CH3:10]

참가 물질

7

반응물 6

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 433294Lithium ChlorideHCID 138003704-Methylheptanoic acid, (-)-

생성물 1

HCID 57160957(4R,5S)-4-Methyl-3-((R)-4-methyl-heptanoyl)-5-phenyl-oxazolidin-2-one

실험 절차

To the acid 99 (19 g, 0.132 mol) and triethylamine (49.9 g, 0.494 mol) in THF (500 mL) at 0° C. was added trimethylacetylchloride (20 g, 0.17 mol). After 1 hour LiCl (7.1 g, 0.17 mol) was added followed by the oxazolidinone (30 g, 0.17 mol). The mixture was warmed to room temperature and after 16 hours the filtrate was removed by filtration and the solution concentrated under reduced pressure. Flash chromatography (7:1 hexane/EtOAc) gave the product 100 as an oil. 31.5 g; 79%. [α]D=5.5 (c 1 in CHCl3). MS, m/z (relative intensity): 304 [M+H, 100%].

후처리

  1. customwas removed by filtration
  2. concentrationthe solution concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-88ba7e4358194705b09b2c3f5473d2bc
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642398B2

반응 노트

불러오는 중…