Ammonium Chloride → (3S,5R)-5-Methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-octanoic acid tert-butyl ester

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Reaktionsgleichung

[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:22])[CH2:15][CH2:16][C@H:17]([CH3:21])[CH2:18][CH2:19][CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:33]([O:37][C:38](=[O:41])[CH2:39]Br)([CH3:36])([CH3:35])[CH3:34].[Cl-].[NH4+]>C1COCC1>[C:33]([O:37][C:38](=[O:41])[CH2:39][C@@H:15]([C:14]([N:3]1[C@H:2]([CH3:1])[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4]1=[O:13])=[O:22])[CH2:16][C@H:17]([CH3:21])[CH2:18][CH2:19][CH3:20])([CH3:36])([CH3:35])[CH3:34]

Komponenten

Reaktionsbedingungen

Temperatur: -50 °C

Versuchsvorschrift

To oxazolidinone 100 (12.1 g, 0.04 mol) in THF (200 mL) at −50° C. was added NaHMDS (48 mL of a 1 M solution in THF). After 30 t-butylbromoacetate (15.6 g, 0.08 mol) was added. The solution was stirred for 4 hours at −50° C. and then warmed to room temperature. After 16 hours a saturated aqueous solution of ammonium chloride was added and the two layers separated. The aqueous phase was extracted with ether and the combined organic phases dried (MgSO4) and concentrated. Flash chromatography (9:1 hexane/EtOAc) gave the product 101 as a white solid 12 g; 72%. [α]D=30.2 (c 1 in CHCl3). 13C NMR (100 MHz; CDCl3) 176.47, 171.24, 152.72, 133.63, 128.87, 125.86, 80.85, 78.88, 55.34, 39.98, 38.77, 38.15, 37.58, 30.60, 28.23, 20.38, 20.13, 14.50, 14.28.

Aufarbeitung

temperaturewarmed to room temperature
customthe two layers separated
extractionThe aqueous phase was extracted with ether
dry with materialthe combined organic phases dried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-fc10d5b531924f9e822e31be33fb2ccf
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07189747B2

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