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【结 构 式】

【分子编号】45872

【品名】 

【CA登记号】

【 分 子 式 】C27H34N2O7S2

【 分 子 量 】562.70824

【元素组成】C 57.63% H 6.09% N 4.98% O 19.9% S 11.4%

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)

N-protection of the NH group of (I) with Boc2O and NaOH in Et2O yields derivative (II), which is then condensed with compound (III) by means of NaH in DMF to provide (IV). N-deprotection of (IV) by treatment with TFA in CH2Cl2 followed by reductocondensation with N-Boc-4-piperidone (V) in CH2Cl2 in the presence of Na(OAc)3BH affords compound (VI), which is oxidized with NaBO3.4H2O to provide (VII). Boc removal of (VII) by treatment with TFA in CH2Cl2, followed by reaction of the resulting secondary amine with sulfonyl chloride (VIII) in CH2Cl2 in the presence of Et3N, affords propylsulfonamide derivative (IX). Finally, treatment of (IX) with ethyleneglycol (X) in toluene in the presence of HC(OEt)3 and p-TsOH furnishes the target compound.

1 Boyle, C.D.; Chackalamannil, S.; Chen, L.-Y.; et al.; Benzylidine ketal derivatives as M2 muscarinic receptor antagonists. Bioorg Med Chem Lett 2000, 10, 24, 2727.
2 Chackalamannil, S.; Chen, L.-Y.; Boyle, C.D.; et al.; Benzylidene ketal derivatives as M2 muscarinic receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 114.
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) 21497 (4-Fluorophenyl)(4-piperidinyl)methanone; 4-(4-Fluorobenzoyl)piperidine; 4-(p-Fluorobenzoyl)piperidine 56346-57-7 C12H14FNO 详情 详情
(II) 45867 tert-butyl 4-(4-fluorobenzoyl)-1-piperidinecarboxylate C17H22FNO3 详情 详情
(III) 28620 1,3-benzodioxole-5-thiol C7H6O2S 详情 详情
(IV) 45868 tert-butyl 4-[4-(1,3-benzodioxol-5-ylsulfanyl)benzoyl]-1-piperidinecarboxylate C24H27NO5S 详情 详情
(V) 18620 tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone 79099-07-3 C10H17NO3 详情 详情
(VI) 45869   C29H36N2O5S 详情 详情
(VII) 45870   C29H36N2O7S 详情 详情
(VIII) 45871 1-propanesulfonyl chloride;Propanesulfonylchloride;n-Propylsulphonyl chloride;Propylsulfonyl chloride;n-Propanesulfonyl chloride; 10147-36-1 C3H7ClO2S 详情 详情
(IX) 45872   C27H34N2O7S2 详情 详情
(X) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
Extended Information