3-[5-(tert-Butyldimethylsilyloxy)-3-(3,5-dinitrobenzoyl)-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone

Margaret A. Brimble* and Josephine S. O. Park

School of Chemistry, University of Sydney, Eastern Ave, Camperdown, NSW 2006, Australia. Fax: (+61 3) 9351 3329; E-mail: [email protected]

Received: 20 January 2000 / Accepted: 2 February 2000 / Published: 23 February 2000

A mixture of alcohol 1 (104 mg, 0.20 mmol) [1], triethylamine (41 l, 0.30 mmol) and 3,5-dinitrobenzoyl chloride (55 mg, 0.24 mmol) in dichloromethane (2 ml) was stirred for 2 h. at 30ºC. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate (5 ml), extracted into ethyl acetate (2 x 10 ml), washed with water (2 x 5 ml) and dried over sodium sulfate. Removal of the solvent under reduced pressure and purification of the residue by flash chromatography, using light petroleum-ethyl acetate (8:2) as eluent, gave the title compound 2 (110 mg, 78%) as a colourless oil.

[a]_D -40.22 (c 1.217, CHCl₃).

IR (cm^-1, neat): 1783s, 1737s, 1709s, 1389m, 1109m.

¹H NMR (400 MHz, CDCl₃): 0.03, 0.04 (6H, s, SiMe₂), 0.86 (9H, s, Bu^t), 1.19 (3H, d, J_6',5' 6.0 Hz, H6'), 2.09-2.12 (2H, m, H4'), 2.69 (1H, dd, J_gem 13.5 and J 9.4 Hz, CHCH^APh), 3.20 (1H, dd, J_gem 13.5 and J 3.3 Hz, CHCH^BPh), 3.96-4.00 (1H, m, H5'), 4.12 (1H, dd, J_gem 9.1 and J_5A,4 7.7 Hz, H5^A), 4.17 (1H, dd, J_gem 9.1 and J_5B,4 2.8 Hz, H5^B), 4.62-4.65 (1H, m, H4), 4.66 (1H, d, J_gem 11.4 Hz, OCH^APh), 4.73 (1H, d, J_gem 11.4 Hz, OCH^BPh), 5.56 (1H, d, J_2',3' 4.0 Hz, H2'), 5.70-5.73 (1H, m, H3'), 7.17-7.38 (10H, m, Ph), 9.13 (2H, d, J 2.1 Hz, PhNO₂), 9.21 (1H, t, J 2.1 and J 2.1 Hz, PhNO₂).

¹³C NMR (100 MHz, CDCl₃): -4.8, -4.4 (CH₃, SiMe₂), 18.0 (quat., CMe₃), 23.4 (CH₃, C6'), 25.8 (CH₃, CMe₃), 37.5 (CH₂, CHCH₂Ph), 39.7 (CH₂, C4'), 55.6 (CH, C4), 65.6 (CH₂, C5), 66.6 (CH, C5'), 73.4 (CH, C3'), 73.5 (CH₂, OCH₂Ph), 77.9 (CH, C2'), 122.4, 127.5, 128.2, 128.4, 128.5, 129.0, 129.4, 129.5 [CH, 3 x Ph (last 5 peaks coincidental)], 133.8 (quat., CHCH₂Ph), 134.7 (quat., OC=OC), 136.9 (quat., OCH₂Ph), 148.7 (quat., CNO₂), 152.9 (quat., C2) 161.5 (quat., OC=O), 169.2 (quat., C1').

CI-MS: (FAB, NBA matrix) 722 (MH⁺, 2%), 664 (4), 614 (MH⁺-HOCH₂Ph, 1), 590 (MH⁺-HOSiMe₂Bu^t, 4), 269 (5), 195 (C₇H₃N₂O₅, 4), 91 (CH₂Ph, 100), 73 (48).

Anal. calc. for C₃₆H₄₃N₃O₁₁Si MH⁺ (CI, NH₃), 722.2732; found MH⁺, 722.2745.

Reference

1.	Brimble, M. A.; Park, J. S. O. J. Chem. Soc. Perkin Trans. I 2000, 697-709.

Sample availability: available from the authors.

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