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【结 构 式】

【分子编号】28693

【品名】(4S)-4-(methoxymethyl)-1,3-dioxolan-2-one

【CA登记号】

【 分 子 式 】C5H8O4

【 分 子 量 】132.11612

【元素组成】C 45.46% H 6.1% O 48.44%

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:(XVII)

2) Synthesis of Oxazolidinone (II): 2a) The reaction of 4-benzyloxyaniline (IX) with 1,4-dioxaspiro[4.5]decan-2(S)-ylmethyl methanesulfonate (X) by means of TEA at 140 C gives 3-(4-benzyloxyphenylamino)propane-1,2(R)-diol (XI), which is cyclized with diethyl carbonate and sodium methoxide in refluxing toluene, yielding 3-(4-benzyloxyphenyl)-5(R)-(hydroxymethyl)oxazolidin-2-one (XII). The methylation of (XII) with dimethyl sulfate, NaOH and tetrabutylammonium bisulfate in hot toluene/water affords the corresponding methoxymethyl derivative (XIII). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in ethanol/dichloromethane to give oxazolidinone (II). 2b) The methylation of 4(S)-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (XIV) with dimethyl sulfate and NaOH gives 4(S)-(methoxymethyl)-2,2-dimethyl-1,3-dioxolane (XV), which is hydrolyzed with hot aqueous HCl to 3-methoxypropane-1,2(R)-diol (XVI). The cyclization of (XVI) with diethyl carbonate by means of NaH affords 4(S)-(methoxymethyl)-1,3-dioxolan-2-one (XVII) (2, 5). The condensation of (XVII) with N-(4-benzyloxyphenyl)carbamic acid methyl ester (XVIII) (obtained by reaction of 4-benzyloxyaniline (IX) with methyl chloroformate) by means of K2CO3 at 160 C provides the protected oxazolidinone (XIII), which is finally debenzylated as before to give oxazolidinone (II).

1 Castaner, J.; Sorbera, L.A.; Rabasseda, X.; Befloxatone. Drugs Fut 1999, 24, 10, 1057.
2 Koenig, J.-J.; Schoofs, A.; Jarreau, F.-X.; Rovei, V. (Laboratoires Delalande); 3-Aryl oxazolidinones, process for their preparation and their therapeutical use. EP 0424243; EP 0424244; EP 0428421; JP 1992502333; JP 1992502334; JP 1992502335; US 5036090; US 5036091; US 5171747; US 5196543; WO 9105775 .
3 Jarreau, F.-X.; Koenig, J.-J.; Rovei, V. (Laboratoires Delalande); 3-Aryl-oxazolidinone derivs., process for their preparation and their use in therapeutics. EP 0511031; FR 2675504; JP 1993112542; US 5264443 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II) 28682 (5R)-3-(4-hydroxyphenyl)-5-(methoxymethyl)-1,3-oxazolidin-2-one C11H13NO4 详情 详情
(IX) 22460 4-(benzyloxy)aniline; 4-(benzyloxy)phenylamine C13H13NO 详情 详情
(X) 28688 (2R)-1,4-dioxaspiro[4.5]dec-2-ylmethyl methanesulfonate C10H18O5S 详情 详情
(XI) 28689 (2R)-3-[4-(benzyloxy)anilino]-1,2-propanediol C16H19NO3 详情 详情
(XII) 28695 (5R)-3-[4-(benzyloxy)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one C17H17NO4 详情 详情
(XIII) 28690 (5R)-3-[4-(benzyloxy)phenyl]-5-(methoxymethyl)-1,3-oxazolidin-2-one C18H19NO4 详情 详情
(XIV) 12709 [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol 22323-82-6 C6H12O3 详情 详情
(XV) 28691 (4S)-4-(methoxymethyl)-2,2-dimethyl-1,3-dioxolane C7H14O3 详情 详情
(XVI) 28692 (2R)-3-methoxy-1,2-propanediol C4H10O3 详情 详情
(XVII) 28693 (4S)-4-(methoxymethyl)-1,3-dioxolan-2-one C5H8O4 详情 详情
(XVIII) 28694 methyl 4-(benzyloxy)phenylcarbamate C15H15NO3 详情 详情
Extended Information