Synthesis of [2H4]oxymetazoline and [14C]oxymetazoline

被引:0
|
作者
Brugger, Michelle L. [1 ]
Borges, Scott [1 ]
Ren, Sumei [1 ]
McNamara, Paul [1 ]
机构
[1] Merck & Co Inc, Merck Res Labs, Kenilworth, NJ 07033 USA
来源
关键词
H-2(4)]oxymetazoline; C-14]oxymetazoline; Afrin; SCH; 9384; carbon-14; synthesis; AROMATIC-COMPOUNDS; BROMOMETHYLATION; ACIDS;
D O I
10.1002/jlcr.1805
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
An efficient synthesis of [H-2(4)] and [C-14]oxymetazoline has been developed. Both compounds follow the same synthetic route with the introduction of the label occurring at different synthetic steps. The synthesis of [H-2(4)]oxymetazoline from [H-2(4)]ethylene diamine was achieved in one step with a 40% yield. The synthesis of [C-14]oxymetazoline from potassium [C-14]cyanide was achieved in two steps with an overall radiochemical yield of 67%.
引用
收藏
页码:793 / 800
页数:8
相关论文
共 50 条
  • [1] Synthesis of 3H, 14C and 2H4 labelled SCH 211803
    Hesk, D.
    Voronin, K.
    Mcnamara, P.
    Royster, P.
    Koharski, D.
    Hendershot, S.
    Saluja, S.
    Truong, V.
    Chan, T. M.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2007, 50 (1-2): : 131 - 137
  • [2] Synthesis of a delta opioid agonist in [2H6], [2H4], [11C], and [14C] labeled forms
    Elmore, Charles S.
    Brush, Kelly
    Schou, Magnus
    Palmer, William
    Dorff, Peter N.
    Powell, Mark E.
    Hoesch, Valerie
    Hall, James E.
    Hudzik, Thomas
    Halldin, Christer
    Dantzman, Cathy L.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2011, 54 (14): : 847 - 854
  • [3] Synthesis of 3H, 2H4, and 14C-MK 3814 (preladenant)
    Hesk, D.
    Borges, S.
    Dumpit, R.
    Hendershot, S.
    Koharski, D.
    McNamara, P.
    Ren, S.
    Saluja, S.
    Truong, V.
    Voronin, K.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2017, 60 (04): : 194 - 199
  • [4] Synthesis of 3H, 2H4 and 14C-SCH 417690 (Vicriviroc)
    Hesk, D.
    Borges, S.
    Hendershot, S.
    Koharski, D.
    McNamara, P.
    Ren, S.
    Saluja, S.
    Truong, V.
    Voronin, K.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2016, 59 (05): : 190 - 196
  • [5] SYNTHESIS OF [2H4]; [3H]; AND [14C] SCH 900875: A POTENT CXCR3 ANTAGONIST WITH POTENTIAL THERAPEUTIC USE IN THE TREATMENT OF PSORIASIS
    Galliford, Chris V.
    Voronin, Kimberly
    Smith, Amy
    Koharski, David
    Truong, Van
    Borges, Scott
    Lavey, Carolee Flader
    Hesk, David
    Mcnamara, Paul
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (5-6): : 388 - 391
  • [6] Syntheses of [14C] and [2H4]PD0205520, an inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor
    Zhang, YS
    Huang, Y
    Huang, CC
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2005, 48 (07): : 485 - 496
  • [7] Synthesis of [3H] and [14C]genipin
    Queen, Adele E.
    Hesk, David
    Lindsay, David M.
    Kerr, William J.
    Rehder, Kenneth
    Fennell, Tim
    Mascarella, Wayne
    Zhong, Desong
    Runyon, Scott
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2020, 63 (04): : 196 - 202
  • [8] Synthesis of PNU-159548 labelled with 14C and 2H
    Felicini, C
    Fontana, E
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2002, 45 (07): : 543 - 550
  • [9] [14C]Dimethyltitanocene and [14C]Methyl(methyltrimethylsilyl) titanocene - Reagents for the [14C]olefination of carbonyl compounds: synthesis of [14C]Aprepitant
    Wallace, M. A.
    Dean, D. C.
    Melillo, D. G.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2009, 52 (11-12): : 514 - 517
  • [10] Enzymatic synthesis of [14C]ceramide, [14C] glycosphingolipids, and ω-aminoceramide
    Ito, M
    Mitsutake, S
    Tani, M
    Kita, K
    SPHINGOLIPID METABOLISM AND CELL SIGNALING, PT A, 2000, 311 : 682 - 689