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【结 构 式】

【分子编号】27229

【品名】3-(Tert-butoxycarbonylamino)-3-methyl butyric acid ethoxycarbonyl anhydride

【CA登记号】

【 分 子 式 】C13H23NO6

【 分 子 量 】289.32876

【元素组成】C 53.97% H 8.01% N 4.84% O 33.18%

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:(II)

The intermediate N-Boc-amino acid (VII) was synthesized as shown in Scheme 25409101a. Treatment of 3-(tert-butoxycarbonylamino)-3-methylbutanoic acid (I) with ethyl chloroformate and Et3N, followed by reduction of the resulting mixed anhydride (II) with LiBH4, provided alcohol (III). Then, oxidation of (III) under Swern conditions yielded aldehyde (IV). Subsequent Horner-Emmons condensation of (IV) with triethyl phosphonoacetate (V) in the presence of potassium tert-butoxide gave ester (VI), which was saponified with LiOH to provide the required carboxylic acid (VII).

1 Hansen, T.K.; Ankersen, M.; Hansen, B.S.; Raun, K.; Nielsen, K.K.; Lau, J.; Peschke, B.; Lundt, B.F.; Thogersen, H.; Johansen, N.L.; Madsen, K.; Andersen, P.H.; Novel orally active growth hormone secretagogues. J Med Chem 1998, 41, 19, 3705.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11229 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate 541-41-3 C3H5ClO2 详情 详情
29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(I) 22193 3-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid C10H19NO4 详情 详情
(II) 27229 3-(Tert-butoxycarbonylamino)-3-methyl butyric acid ethoxycarbonyl anhydride C13H23NO6 详情 详情
(III) 22194 tert-butyl 3-hydroxy-1,1-dimethylpropylcarbamate C10H21NO3 详情 详情
(IV) 22195 tert-butyl 1,1-dimethyl-3-oxopropylcarbamate C10H19NO3 详情 详情
(V) 10019 Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate 867-13-0 C8H17O5P 详情 详情
(VI) 27230 ethyl (E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoate C14H25NO4 详情 详情
(VII) 22191 (E)-5-[(tert-butoxycarbonyl)amino]-5-methyl-2-hexenoic acid C12H21NO4 详情 详情
Extended Information