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

HRID 458030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458030
[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]

Komponenten

7

Edukt 6

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

Produkt 1

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

Versuchsvorschrift

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%].

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9c7347a96ef448f79ecd912e99bfbc70
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189747B2

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