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【结 构 式】

【分子编号】39830

【品名】methanesulfenyl chloride

【CA登记号】5813-48-9

【 分 子 式 】CH3ClS

【 分 子 量 】82.55352

【元素组成】C 14.55% H 3.66% Cl 42.95% S 38.84%

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:(D)

The reaction of the Schift base (XV) phenyllithium and CH3SCl (D) in DMF gives the corresponding methylthio derivative (XVI), which is debenzylated with 2,4-DNPH p-toluenesulfonate in ethanol yielding p-methoxybenzyl-7beta-amino-7alpha-thiomethyl-3-acetoxymethyl-3-cephem-4-carboxylate (XVII). The acylation of (XVII) with 2-thienylacetyl chloride (E) / pyridine in CH2Cl2 provided the corresponding 2-thienylacetamido derivative (XVIII), which by methanolysis in the presence of thallium trinitrate gives the 7alpha-methoxy derivative (XIX). The p-methoxybenzyl ester of (XIX) is cleaved with TFA-anisole affording 7alpha-methoxycephalothin-(7alpha-methoxy-7-(2-thienylacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid) (XX), which is deacetylated with citrus acetyl enzyme yielding the corresponding hydroxymethyl compound (XXI). Finally, this compound is treated with chlorosulfonyl isocyanate in THF or acetonitrile.

1 Ratcliffe, R.W.; Christensen, B.G.; Total synthesis of beta-lactam antibiotics. III. (rac)-Cefoxitin. Tetrahedron Lett 1973, 46, 4653-56.
2 Castaner, J.; Loren, J.G.; Cefoxitin. Drugs Fut 1978, 3, 6, 434.
3 Christensen, B.G.; Ratcliffe, R.W. (Merck & Co., Inc.); 7-Azido-cephalosporin compounds and their preparation. DE 2365406; FR 2182953; GB 1424373; JP 49014488 .
4 Christensen, B.G.; Cama, L.D. (Merck & Co., Inc.); Antibiotics and processes for their production. DE 2203653; FR 2161866; GB 1350772 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(E) 15673 2-(2-thienyl)acetyl chloride; 2-Thiopheneacetyl chloride 39098-97-0 C6H5ClOS 详情 详情
(D) 39830 methanesulfenyl chloride 5813-48-9 CH3ClS 详情 详情
(XV) 39829 4-methoxybenzyl (6R,7R)-3-[(acetoxy)methyl]-7-[[(E)-(4-nitrophenyl)methylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C25H23N3O8S 详情 详情
(XVI) 39831 4-methoxybenzyl (6R,7S)-3-[(acetoxy)methyl]-7-(methylsulfanyl)-7-[[(E)-(4-nitrophenyl)methylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C26H25N3O8S2 详情 详情
(XVII) 39832 4-methoxybenzyl (6R,7S)-3-[(acetoxy)methyl]-7-amino-7-(methylsulfanyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C19H22N2O6S2 详情 详情
(XVIII) 39833 4-methoxybenzyl (6R,7S)-3-[(acetoxy)methyl]-7-(methylsulfanyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C25H26N2O7S3 详情 详情
(XIX) 39834 4-methoxybenzyl (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C25H26N2O8S2 详情 详情
(XX) 39835 (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C17H18N2O7S2 详情 详情
(XXI) 39836 (6R,7S)-3-(hydroxymethyl)-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C15H16N2O6S2 详情 详情
Extended Information