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

HRID 130533ノート

反応式

HRID 130533 の反応式
[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]

参加物

7

反応物 6

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

生成物 1

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

実験手順

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%].

後処理

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

出典と根拠

ORDレコード
ord-b548da7b618746c2934a0d300d158ff8
出典データセット
uspto-grants-2008_06
特許番号
US07381747B2

反応ノート

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