• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】21520

【品名】2-methoxy-2-methylpropanamide

【CA登记号】

【 分 子 式 】C5H11NO2

【 分 子 量 】117.14788

【元素组成】C 51.26% H 9.46% N 11.96% O 27.31%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

This compound can be prepared by two different ways: 1) The dehydration of 2-amino-2-methylpropranol (I) with H2SO4 at 170-200 C gives 2,2-dimethylazirine (II), which by reaction with methanol by means of boron trifluoride - methanol complex and fractional distillation affords 2-methoxy-2-methylpropylamine (III). The reaction of (III) with formic acid in acetic anhydride yields N-(2-methoxy-2-methylpropyl)formamide (IV), which by reaction with diphosgene (trichloromethyl chloroformate) and triethylamine in dichloromethane gives 2-methoxy-2-methylpropylisonitrile (MIBI) (V). Finally, this compound or its CuBF4 complex Cu(MIBI)4BF4 is treated with 99mTcO4 (VI) and sodium dithionite or formamide sulfinic acid respectively, in ethanol - water. 2) The methylation of methyl 2-hydroxyisobutylrate (VII) with NaH - methyl iodide in DMF - THF gives methyl 2-methoxy-2-methylpropanoate (VIII), which by reaction with ammonia is converted to the corresponding amide (IX). Finally, this compound is reduced with LiAlH4 in THF yielding the amine (III), already obtained.

1 Bergstein, P.L.; Subramanyam, V. (E.I. Du Pont de Nemours & Co.); Ether isonitriles and radilabeled complexes thereof. AU 8666842; EP 0233368; JP 87201363 .
2 Williams, S.; Okada, R.D.; Gaffney, T.; Glover, D.; Myocardial kinetics of technetium-99m-hexakis-2-methoxy-2-methylpropyl-isonitrile. Circulation 1988, 77, 491.
3 Carrell, S.A.; Robinson, C.P.; Prous, J.; Castaner, J.; TECHNETIUM [(99m)Tc] SESTAMIBI < Prop INN; BAN >. Drugs Fut 1989, 14, 12, 1169.
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) 21513 2-amino-2-methyl-1-propanol;Karl Fischer;2-Amino-2-methyl-propan-1-ol;2-amino-2-methyl-1-propanol 124-68-5 C4H11NO 详情 详情
(II) 21514 2,2-dimethylaziridine C4H9N 详情 详情
(III) 21515 2-methoxy-2-methyl-1-propanamine C5H13NO 详情 详情
(IV) 21516 2-methoxy-2-methylpropylformamide C6H13NO2 详情 详情
(V) 21517 2-Methoxy-2-methylpropyl isocyanide C6H11NO 详情 详情
(VII) 21518 methyl 2-hydroxy-2-methylpropanoate 2110-78-3 C5H10O3 详情 详情
(VIII) 21519 methyl 2-methoxy-2-methylpropanoate C6H12O3 详情 详情
(IX) 21520 2-methoxy-2-methylpropanamide C5H11NO2 详情 详情
Extended Information