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Synlett
Volumn , Issue 1, 2007, Pages 136-140
Effective pathway to the α-CF3-substituted azahistidine analogues
Author keywords

Amino acids; Click reaction; Fluorinated imines; Histidine; Organic azides
Indexed keywords

ALPHA PROPARGYL ALPHA TRIFLUOROMETHYL ALPHA AMINO ESTER; ALPHA TRIFLUOROMETHYL ALPHA AZAHISTIDINE DERIVATIVE; AZIDE; BROMIDE; ESTER DERIVATIVE; HISTIDINE DERIVATIVE; IMINE; MAGNESIUM; PYRUVIC ACID DERIVATIVE; TRIFLUOROPYRUVATE; UNCLASSIFIED DRUG;
EID: 33846439383     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956492     Document Type: Article
Times cited : (27)
References (42)
  • 5
    • 33846416444 scopus 로고
    • Kukhar, V. P, Soloshonok, V. A, Eds, John Wiley and Sons Ltd, New York
    • (a) Sewald, N.; Burger, K. In Synthesis of β-Fluoro-Containing Amino Acids; Kukhar', V. P.; Soloshonok, V. A., Eds.; John Wiley and Sons Ltd.: New York, 1995, 139.
    • (1995) Synthesis of β-Fluoro-Containing Amino Acids , pp. 139
    • Sewald, N.1    Burger, K.2
  • 10
    • 0002976015 scopus 로고
    • Filler, R, Kobayashi, Y, Eds, Kondasha, Tokyo and Elsevier Biomedical Press: Amsterdam, and references cited therein
    • Kollonitsch, J. In Biomedicinal Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y., Eds.; Kondasha, Tokyo and Elsevier Biomedical Press: Amsterdam, 1982, 93; and references cited therein.
    • (1982) Biomedicinal Aspects of Fluorine Chemistry , pp. 93
    • Kollonitsch, J.1
  • 34
    • 33846407873 scopus 로고    scopus 로고
    • General Procedure for the Preparation of 2. Allenylmagnesiumbromide17 (solution in THF, 10.0 mmol) was added dropwise to a stirred solution of an imine (10.0 mmol) in dry THF (25 mL) at-78 °C. After 1 h at -78 °C the reaction mixture was allowed to warm to r.t. within 2 h. The reaction was quenched with 1 N HCl and extracted with Et 2O (2 × 25 mL, The combined organic layer was washed with brine (25 mL, dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography (EtOAc-PE, Data for Compounds 2a,b. Compound 2a: oil. 1H NMR (300 MHz, CDCl3, δ, 2.09 (s, 1 H, CH, 3.10 (d, JAB, 16.6Hz, 1 H, CH2, 3.71 (d, JAB, 16.6 Hz, 1 H, CH2, 3.96 (s, 3 H, OCH3, 5.22 (m, 2 H, OCH2, 6.10 (s, 1 H, NH, 7.43 (m, 5 H, Ph, 19F NMR 282 MHz, CDCl3
    • 4: C, 48.81; H, 5.47; N, 4.74. Found: C, 48.74; H, 5.47; N, 4.68.
  • 41
    • 33846452056 scopus 로고    scopus 로고
    • Typical Procedure for the Preparation of 3. Method A. A mixture of organic azide (1.0 mmol, amino ester 2 (1.0 mmol, DIPEA (3.0 mmol) and CuI (0.1 mmol) in THF (10 mL) was stirred at r.t. for 6-8 h. The resulted reaction mixture was treated with 1 N HCl (15 mL, and extracted with Et2O (3 × 15 mL, Combined organic layers were dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (EtOAc-PE, Method B. Organic azide (2.0 mmol) and amino ester 2 (2.0 mmol) were suspended in 1:1 H2O-t-BuOH (8 mL, To this was added CuSO4-5H2O (5 M solution, 0.1 mmol, 5 mol, and sodium ascorbate (0.6 mmol, The mixture was stirred at r.t. for 24 h, at which time TLC (silica, PE-EtOAc) indicated complete conversion. The resulted solution was concentrated under reduced pressure rotary evaporator, The residue was dissolved in 30 mL of
    • 13: C, 49.58; H, 4.73; N, 7.97. Found: C, 49.12; H, 4.57; N, 7.57.
  • 42
    • 33846459915 scopus 로고    scopus 로고
    • Data for Compound 6. Mp 216-217 °C. 1H NMR (300 MHz, D2O, δ, 3.38 (d, JAB, 15.3 Hz, 1 H, 3.64 (d, JAB, 15.3 Hz, 1 H, 7.73 (s, 1 H, H-triazole, 19F NMR (282 MHz, D2O, δ (TFA, 3.55 (s, 3 F, CF3, 13CNMR (150.9 MHz, D2O, δ, 26.5,65.3 (q, 2JC-F, 25.4 Hz, 123.5 q, 1JC-F, 228.9 Hz, 128.1, 137.9, 166.0. Anal. Calcd for C 6H7F4N4O2: C, 32.15; H, 3.15; N, 25.00. Found: C, 32.12; H, 3.04; N, 24.67
    • 2: C, 32.15; H, 3.15; N, 25.00. Found: C, 32.12; H, 3.04; N, 24.67.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.