methoxymethyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】40165

【品名】methoxymethyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

【CA登记号】

【分子式】C₁₀H₁₆N₂O₄S

【分子量】260.31412

【元素组成】C 46.14% H 6.2% N 10.76% O 24.58% S 12.32%

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：(III)

The esterification of potassium phenoxymethylpenicillanate (I) with chloromethyl methyl ether (A) in methylene chloride-THF gives the methoxymethyl ester of penicilline V (II), which is then treated with dimethylaniline (B) in CH2Cl2 to afford methoxymethyl 6-aminopenicillanate (III). Finally, this product is condensed with phenylglycyl chloride (C) hydrochloride and acetone (D) by means of NaOH.

参考文献中间体

合成目标

【1】 Sleezer, P.D.; Johnson, D.A. (Bristol-Myers Squibb Co.); Antibacterial agents. DE 2244915; ES 406644; FR 2154488; GB 1400584; JP 48036186 .
【2】 Playle, A.C.; Castaner, J.; Sarpicillin. Drugs Fut 1977, 2, 7, 478.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	17036	N,N-dimethyl-N-phenylamine; N,N-dimethylbenzenamine; N,N-dimethylaniline	121-69-7	C₈H₁₁N	详情	详情
(A)	18319	Chloro(methoxy)methane; Chloromethyl methyl ether	107-30-2	C₂H₅ClO	详情	详情
(D)	23199	2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether	67-64-1	C₃H₆O	详情	详情
(I)	40163	potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	132-98-9	C₁₆H₁₇KN₂O₅S	详情	详情
(II)	40164	methoxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate		C₁₈H₂₂N₂O₆S	详情	详情
(III)	40165	methoxymethyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate		C₁₀H₁₆N₂O₄S	详情	详情
(IV)	40166	methoxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate		C₁₈H₂₃N₃O₅S	详情	详情
(C)	40055	(2R)-2-amino-2-phenylethanoyl chloride		C₈H₈ClNO	详情	详情

Extended Information