2-chloroacetaldehyde -Drug Synthesis Database

【结构式】

【分子编号】47061

【品名】2-chloroacetaldehyde

【CA登记号】107-20-0

【分子式】C₂H₃ClO

【分子量】78.49792

【元素组成】C 30.6% H 3.85% Cl 45.16% O 20.38%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

Chloroacetaldehyde (VII), prepared by acid hydrolysis of the dimethyl ketal (VI), was condensed with ethyl acetoacetate (VIII) to produce ethyl 2-methyl-3-furoate (IX). Basic hydrolysis of ester (IX), followed by chlorination of the resultant carboxylic acid (X) with SOCl2, gave acid chloride (XI). Then, condensation of amine (V) with acid chloride (XI) yielded amide (XII), which was finally converted to the title thioamide by treatment with Lawesson's reagent in hot toluene.

参考文献中间体

合成目标

【1】 Brouwer, W.G.; Osika, E.M.; Pierce, B.J. (Uniroyal Chemical Company, Inc.); Furan- and thiophenecarbothioamide derivs., their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants. EP 0874839; JP 1999504657; US 5696151; WO 9719940 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	56030	4-chloro-3-[(3-methyl-2-butenyl)oxy]phenylamine; 4-chloro-3-[(3-methyl-2-butenyl)oxy]aniline		C₁₁H₁₄ClNO	详情	详情
(VI)	56031	1-chloro-2,2-dimethoxyethane; 2-Chloro-1,1-dimethoxyethane; Chloroacetaldehyde dimethyl acetal; Dimethyl chloroacetal; Methyl Chloroacetal	97-97-2	C₄H₉ClO₂	详情	详情
(VII)	47061	2-chloroacetaldehyde	107-20-0	C₂H₃ClO	详情	详情
(VIII)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(IX)	56032	Ethyl- 2-methyl-3-furoate	28921-35-9	C₈H₁₀O₃	详情	详情
(X)	56033	2-Methyl-3-furoic acid	6947-94-0	C₆H₆O₃	详情	详情
(XI)	56034	2-methyl-3-furoyl chloride	5555-00-0	C₆H₅ClO₂	详情	详情
(XII)	56035	N-{4-chloro-3-[(3-methyl-2-butenyl)oxy]phenyl}-2-methyl-3-furamide		C₁₇H₁₈ClNO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Coupling of carboxylic acid (II) to the 7-aminocephem derivative (I) using POCl3 and pyridine produced the corresponding amide (III). Displacement of the chloro group of (III) with triphenyl phosphine furnished the phosphonium salt (IV), which was subjected to a Wittig reaction with chloroacetaldehyde (V), yielding the Z-propenyl chloride (VI). Subsequent reaction of allyl chloride (VI) with 4-amino-2-mercapto-6-methylpyrimidine (VII) in the presence of NaI produced the E-propenyl sulfide (VIII). The N-trityl group and the p-methoxybenzyl ester of (VIII) were finally cleaved by treatment with trifluoroacetic acid in anisole to furnish the title compound.

参考文献中间体

合成目标

【1】 Lee, C.-S.; et al.; Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins. J Antibiot 2000, 53, 11, 1305.

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)	26869	4-methoxybenzyl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₁₆H₁₇ClN₂O₄S	详情	详情
(II)	25058	2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid	64485-90-1	C₂₅H₂₁N₃O₃S	详情	详情
(III)	25062	4-methoxybenzyl 3-(chloromethyl)-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₄₁H₃₆ClN₅O₆S₂	详情	详情
(IV)	47060	[[2-[[(4-methoxybenzyl)oxy]carbonyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl](triphenyl)phosphonium chloride		C₅₉H₅₁ClN₅O₆PS₂	详情	详情
(V)	47061	2-chloroacetaldehyde	107-20-0	C₂H₃ClO	详情	详情
(VI)	47062	4-methoxybenzyl 3-[(Z)-3-chloro-1-propenyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₄₃H₃₈ClN₅O₆S₂	详情	详情
(VII)	47063	2-amino-6-methyl-4-pyrimidinethiol; 2-amino-6-methyl-4-pyrimidinylhydrosulfide		C₅H₇N₃S	详情	详情
(VIII)	47064	4-methoxybenzyl 3-[(E)-3-[(2-amino-6-methyl-4-pyrimidinyl)sulfanyl]-1-propenyl]-7-([2-(methoxyimino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₄₈H₄₄N₈O₆S₃	详情	详情

Extended Information