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【结 构 式】

【分子编号】23004

【品名】benzhydryl 2-[3,4-bis(acetoxy)phenyl]-2-bromoacetate

【CA登记号】

【 分 子 式 】C25H21BrO6

【 分 子 量 】497.34214

【元素组成】C 60.38% H 4.26% Br 16.07% O 19.3%

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:(IV)

The bromination of 3,4-diacetoxyphenylacetic acid with N-bromosuccinimide (NBS) and SOCl2 gives the corresponding bromoacetic acid (II), which is esterified with diphenyldiazomethane (III) in acetone affording the diphenylmethyl ester (IV). The reaction of (IV) with N-hydroxyphthalimide (V) by means of triethylamine in acetonitrile yields diphenylmethyl-2-phthalimidooxy-2-(3,4-diacetoxy phenyl)acetate (VI), which is treated witb methyl hydrazine in dichloromethane to give diphenylmethyl-2-aminooxy-2-(3,4-diacetoxyphenyl)acetate (VII). The condensation of (VII) with (2-triphenylmethylamino-4-thiazolyl)glyoxylic acid (VIII) in methanol affords 2-(2-triphenylmethylamino-4-thiazolyl)-2-[(Z)-(diphenyl)methoxyimino]acetic acid (IX), which is condensed with 7beta-amino-3-[2-(diphenylmethoxycarbonyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-ylthiomethyl]-3-cephem-4-carboxylic acid diphenylmethyl ester (X) by means of dicyclohexylcarbodiimide (DCC) in dichloromethane giving the protected final product (XI). Finally, this compound is deprotected by treatment first with trifluoroacetic acid and then with NaHCO3 in water.

1 Ohnishi, H.; Kosuzume, H.; Mizota, M.; Suzuki, Y.; Mochida, E. (Mochida Pharmaceutical Co., Ltd.); Cephalosporin derivs.. AU 8654876; AU 8655860; EP 0197409; EP 0359291; JP 1987077392; JP 1987161793; JP 1987167784; US 4840945; US 5001121; WO 8605786 .
2 Prous, J.; Castaner, J.; M-14659. Drugs Fut 1988, 13, 12, 1047.
3 Kusakabe, S.; Kosuzume, H.; Kato, K.; Shiihara, T.; Murakami, K.; Yamada, H.; Ishigura, J.; Oikawa, Y.; Mochizuki, H.; Antibacterial and pharmacokinetic properties of M1. J Antibiot 1988, 41, 3, 377.
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) 23001 2-[3,4-bis(acetoxy)phenyl]acetic acid C12H12O6 详情 详情
(II) 23002 2-[3,4-bis(acetoxy)phenyl]-2-bromoacetic acid C12H11BrO6 详情 详情
(III) 23003 Diphenyldiazomethane C13H10N2 详情 详情
(IV) 23004 benzhydryl 2-[3,4-bis(acetoxy)phenyl]-2-bromoacetate C25H21BrO6 详情 详情
(V) 13505 N-Hydroxyphthalimide; 2-Hydroxy-1H-isoindole-1,3(2H)-dione 524-38-9 C8H5NO3 详情 详情
(VI) 23006 benzhydryl 2-[3,4-bis(acetoxy)phenyl]-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]acetate C33H25NO9 详情 详情
(VII) 23007 benzhydryl 2-(aminooxy)-2-[3,4-bis(acetoxy)phenyl]acetate C25H23NO7 详情 详情
(VIII) 23008 2-oxo-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid C24H18N2O3S 详情 详情
(IX) 23009 2-([2-(benzhydryloxy)-1-[3,4-bis(acetoxy)phenyl]-2-oxoethoxy]imino)-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid C49H39N3O9S 详情 详情
Extended Information