【结 构 式】 |
【分子编号】37796 【品名】(2R)-2-[(benzyloxy)methyl]-N,N-diethylpentanamide 【CA登记号】 |
【 分 子 式 】C17H27NO2 【 分 子 量 】277.40692 【元素组成】C 73.61% H 9.81% N 5.05% O 11.53% |
合成路线1
该中间体在本合成路线中的序号:(VII)The intermediate (R)-formyl amide (IX) was synthesized as follows. Acylation of the lithium anion of (S)-4-benzyl-2-oxazolidinone (I) with valeryl chloride (II) provided acyl oxazolidinone (III). Subsequent diastereoselective benzyloxymethylation of (III) with chloride (IV) and TiCl4 gave benzyl ether (V). Hydrolysis of (V) with lithium peroxide, followed by coupling of the resulting carboxylic acid (VI) with diethylamine in the presence of TBTU yielded diethylamide (VII). Hydrogenolysis of the benzyl group of (VII) using Pearlman's catalyst afforded alcohol (VIII), which was oxidized to aldehyde (IX) by means of Dess-Martin periodinane or NaOCl in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO) to give (IX).
【1】 Soucy, F.; et al.; A novel and efficient synthesis of a highly active analogue clasto-lactacystin beta-lactone. J Am Chem Soc 1999, 121, 43, 9967. |
【2】 Plamondon, L.; Soucy, F.; Behnke, M.; Roush, W.; Synthesis of clasto-lactacystin beta-lactone and analogs thereof. WO 9909006 . |
【3】 Plamondon, L.; Adams, J.; Elliot, P. (ProScript, Inc.); Proteasome inhibitors, ubiquitin pathway inhibitors or agents that interfere with the activation of NF-kappaB via the ubiquitin proteasome pathway to treat inflammatory and autoimmune diseases. WO 9915183 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 14694 | (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone | 90719-32-7 | C10H11NO2 | 详情 | 详情 |
(II) | 15116 | pentanoyl chloride; valeryl chloride | 638-29-9 | C5H9ClO | 详情 | 详情 |
(III) | 29431 | (4S)-4-benzyl-3-pentanoyl-1,3-oxazolidin-2-one | C15H19NO3 | 详情 | 详情 | |
(IV) | 14560 | Benzyl chloromethyl ether; 1-[(chloromethoxy)methyl]benzene | 3587-60-8 | C8H9ClO | 详情 | 详情 |
(V) | 37794 | (4S)-4-benzyl-3-[(2R)-2-[(benzyloxy)methyl]pentanoyl]-1,3-oxazolidin-2-one | C23H27NO4 | 详情 | 详情 | |
(VI) | 37795 | (2R)-2-[(benzyloxy)methyl]pentanoic acid | C13H18O3 | 详情 | 详情 | |
(VII) | 37796 | (2R)-2-[(benzyloxy)methyl]-N,N-diethylpentanamide | C17H27NO2 | 详情 | 详情 | |
(VIII) | 37797 | (2R)-N,N-diethyl-2-(hydroxymethyl)pentanamide | C10H21NO2 | 详情 | 详情 | |
(IX) | 37798 | (2R)-N,N-diethyl-2-formylpentanamide | C10H19NO2 | 详情 | 详情 |