메뉴 건너뛰기




Volumn , Issue 4, 2008, Pages 539-542

Synthesis of β,β′-diamino acids from α-amino acid derived β-lactams

Author keywords

Amino acids; Amino alcohols; Chiral pool; Diazo compounds; Lactams

Indexed keywords

ALPHA AMINO ACID; AMIDE; AMINO ACID DERIVATIVE; AZETIDINONE DERIVATIVE; BETA LACTAM; ESTER DERIVATIVE; SODIUM AZIDE; THIOXYL DERIVATIVE;

EID: 40949151627     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032079     Document Type: Article
Times cited : (13)

References (40)
  • 1
    • 84879020577 scopus 로고    scopus 로고
    • Taylor, J. B, Triggle, D. J, Eds, Elsevier: Oxford
    • Hubschwerlen, C. In Comprehensive Medicinal Chemistry II, Vol. 7; Taylor, J. B.; Triggle, D. J., Eds.; Elsevier: Oxford, 2006, 479.
    • (2006) Comprehensive Medicinal Chemistry II , vol.7 , pp. 479
    • Hubschwerlen, C.1
  • 2
    • 40949109789 scopus 로고    scopus 로고
    • Matthews, J. L. Synthesis of Peptides and Peptidomimetics, In Methods of Organic Chemistry (Houben-Weyl), E22c; Goodman M., Felix A., Moroder L., Toniolo C.; Thieme: Stuttgart, 2003, 552.
    • (a) Matthews, J. L. Synthesis of Peptides and Peptidomimetics, In Methods of Organic Chemistry (Houben-Weyl), Vol. E22c; Goodman M., Felix A., Moroder L., Toniolo C.; Thieme: Stuttgart, 2003, 552.
  • 4
    • 0003693460 scopus 로고    scopus 로고
    • 2nd ed, Juaristi, E, Soloshonok, V. A, Eds, Wiley: Hoboken
    • (c) Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E.; Soloshonok, V. A., Eds.; Wiley: Hoboken, 2005.
    • (2005) Enantioselective Synthesis of β-Amino Acids
  • 16
    • 84987300083 scopus 로고
    • Chem. Abstr. 1969, 71, 123860.
    • (1969) Chem. Abstr , vol.71 , pp. 123860
  • 18
    • 0004232165 scopus 로고    scopus 로고
    • 2nd ed, Ager, D, Ed, CRC Press LLC: Boca Raton
    • Ager, D. J. In Handbook of Chiral Chemicals, 2nd ed.; Ager, D., Ed.; CRC Press LLC: Boca Raton, 2006, 11.
    • (2006) Handbook of Chiral Chemicals , pp. 11
    • Ager, D.J.1
  • 26
    • 40949144565 scopus 로고    scopus 로고
    • 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.
  • 27
    • 0026537333 scopus 로고    scopus 로고
    • Palomo, C.; Aizpurua, J. M.; Urchegui, R.; Iturburu, M. J. Org. Chem. 1992, 57, 1571; see also ref. 13a.
    • Palomo, C.; Aizpurua, J. M.; Urchegui, R.; Iturburu, M. J. Org. Chem. 1992, 57, 1571; see also ref. 13a.
  • 28
    • 40949135181 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 31
    • 40949161097 scopus 로고    scopus 로고
    • 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
    • 5 (532.07): C, 63.21; H, 7.20; N, 7.90. Found: C, 63.24; H, 7.18; N, 8.15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.