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

HRID 479041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479041
[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-88ba7e4358194705b09b2c3f5473d2bc
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642398B2

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