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【结 构 式】

【分子编号】29768

【品名】sodium 2-ethoxybenzenolate

【CA登记号】

【 分 子 式 】C8H9NaO2

【 分 子 量 】160.148028

【元素组成】C 60% H 5.66% Na 14.36% O 19.98%

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:(B)

Epoxidation of trans-cinnamyl alcohol (A) gives compound (I), which in turn is reacted with sodium 2-ethoxyphenate (B) to give the diol (II). The primary alcoholic group of (II) is reacted with p-nitrobenzoyl chloride to obtain (III), and (IV) is prepared by treatment of (III) with methanesulfonyl chloride. By treatment of (IV) with sodium hydroxide in an aqueous/dioxane solution the epoxide (V) is obtained in high yield, and this reaction causes inversion of configuration at C-2 carbon atom. Treatment of (V) with aqueous methanolic ammonia gives (VI), which in turn is acylated to (VII) with chloroacetyl chloride and cyclized to morpholone (VIII) with potassium tert-butoxide. The reduction to the final compound FCE-20124 is performed with [sodium bis(2-methoxyethoxy)aluminum hydride] (RED-AL) in toluene.

1 Lazzari, E.; Meroni, M.; Mazzini, G.; Melloni, P.; Della Torre, A.; Configurantional studies on 2[gamma-(2-ethoxyphenoxy)benzyl]morpholine FCE-20124. Tetrahedron 1985, 41, 7, 1393.
2 Torre, A.D.; Carniel, G.; Rossi, A.; Melloni, P. (Pharmacia Corp.); Substituted morpholine derivatives and compositions. DE 2901032; FR 2430412; FR 2442839; GB 2014981; JP 54148739; US 4229449 .
3 Riva, F.; FCE-20124. Drugs Fut 1985, 10, 11, 905.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(D) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(A) 13951 (E)-3-Phenyl-2-propen-1-ol 104-54-1 C9H10O 详情 详情
(B) 29768 sodium 2-ethoxybenzenolate C8H9NaO2 详情 详情
(I) 29767 [(2R,3S)-3-phenyloxiranyl]methanol C9H10O2 详情 详情
(II) 29769 (2S,3S)-3-(2-ethoxyphenoxy)-3-phenyl-1,2-propanediol C17H20O4 详情 详情
(III) 29770 (1S,2S)-1-(2-ethoxyphenoxy)-4-(4-nitrophenyl)-1-phenyl-2-butanol C24H25NO5 详情 详情
(IV) 29771 2-ethoxyphenyl (1S,2S)-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-4-(4-nitrobenzyloxy)-1-phenylbutyl ether; [[(1S)-1-[(S)-(2-ethoxyphenoxy)(phenyl)methyl]-3-(4-nitrobenzyloxy)propyl]oxy](methyl)dimethylene-lambda(6)-sulfane C27H31NO6S 详情 详情
(V) 29772 2-ethoxyphenyl (S)-2-oxiranyl(phenyl)methyl ether; 2-[(S)-(2-ethoxyphenoxy)(phenyl)methyl]oxirane C17H18O3 详情 详情
(VI) 29773 (1S,2S)-3-amino-1-(2-ethoxyphenoxy)-1-phenyl-2-propanol C17H21NO3 详情 详情
(VII) 29774 1-[3-[(chlorocarbonyl)amino]-2-hydroxy-1-phenylpropoxy]-2-ethoxybenzene C18H20ClNO4 详情 详情
(VIII) 29775 (6R)-6-[(2-ethoxyphenoxy)(phenyl)methyl]-3-morpholinone C19H21NO4 详情 详情
(C) 18941 p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride 122-04-3 C7H4ClNO3 详情 详情
Extended Information