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40949144565
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Methyl (2R,3S, 1′S)-3-(Benzyloxycarbonylamino)-2, tert- butyloxycarbonylamino)phenylmethyl]butanoate (10) Et3N (100 μL 718 μmol) was added to β-lactam 1a (102 mg, 240 μmol) in anhyd MeOH (7 mL, After stirring for 21 h at r.t, TLC) the volatile components were removed at reduced pressure and the remnant was purified by chromatography (SiO2, n-hexane-EtOAc, 3:1) yielding methyl ester 10 (109 mg, 239 μmol, 99, as a colorless wax: [α]D20 -23.0 (c 1.05, CHCl3, 1H NMR (500 MHz, DMSO-d6, δ, 1.03 (d, 3J, 6.7 Hz, 3 H, 4-H, 1.35 [s, 9 H, C(CH3) 3, 2.89 (dd, 3J, 8.3 Hz, 3J, 6.7 Hz, 1 H, 2-H, 3.49 (s, 3 H, OCH3, 3.54 ddq, 3J, 9.1 Hz, 3J, 7.0 Hz
-
6: 457.2339; found: 457.2344.
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27
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0026537333
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Palomo, C.; Aizpurua, J. M.; Urchegui, R.; Iturburu, M. J. Org. Chem. 1992, 57, 1571; see also ref. 13a.
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28
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40949135181
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CCDC 668750 (27), CCDC 668751 (15), and CCDC 668749 (17) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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CCDC 668750 (27), CCDC 668751 (15), and CCDC 668749 (17) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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40949161097
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2S,3S,1′R, 3-(Benzyloxycarbonylamino)-N-butyl-2, tert-butyloxycarbonylamino)-4-chlorphenylmethyl]-butanamide (24) BuNH 2 (23 μL, 233 μmol) and NaN3 (2 mg, 31 μmol) were added to a solution of β-lactam 2b (81 mg, 176 μmol) in anhyd DMF (1 mL) under argon. The mixture was stirred for 42 h at r.t, TLC, poured into brine (6 mL, and extracted with Et2O (3 x 10 mL, The combined organic layers were dried (MgSO4, concentrated, and purified by chromatography (SiO2, n-hexane-EtOAc, 4:1 → 2:1) yielding 24 (74 mg, 139 μmol, 79, as a colorless solid: mp 176-178°C; [α]D20 +3.9 (c 1.00, CHCl3, 1H NMR (500 MHz, DMSO-d6, δ, 0.72 (t, 3J, 7.2 Hz, 3 H, CH2CH3, 0.86 dtq
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5 (532.07): C, 63.21; H, 7.20; N, 7.90. Found: C, 63.24; H, 7.18; N, 8.15.
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