4-nitrophenyl (2S)-3-(benzoylsulfanyl)-2-methylpropanoate -Drug Synthesis Database

【结构式】

【分子编号】35380

【品名】4-nitrophenyl (2S)-3-(benzoylsulfanyl)-2-methylpropanoate

【CA登记号】

【分子式】C₁₇H₁₅NO₅S

【分子量】345.37584

【元素组成】C 59.12% H 4.38% N 4.06% O 23.16% S 9.28%

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：(VIII)

(S)-3-Benzoylthio-2-methylpropionic acid (VI) was activated as the acid chloride (VII) by treatment with SOCl2 or optionally converted to the active ester (VIII) upon condensation with p-nitrophenol in the presence of DCC. Coupling of aminoacid (V) with either acid chloride (VII) under Schotten-Baumann conditions or with p-nitrophenyl ester (VIII) in the presence of Et3N gave rise to the corresponding amide (IX). The benzoyl thioester of (IX) was finally cleaved employing aqueous ammonia to afford the title thiol.

参考文献中间体

合成目标

【1】 Miyake, Y.; Horiuchi, M.; Mita, S.; Tsuji, F.; Involvement of leukotriene B4 in murine dermatitis models. Biochem Pharmacol 1998, 55, 297.
【2】 Kawashima, Y.; Horiuchi, M. (Santen Pharmaceutical Co., Ltd.); Novel amino acid derivs. having N,N-dialkylaminophenyl group. EP 0870762; JP 1996301840; WO 9627585 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(V)	41582	(2R)-2-amino-3-[[4-(dimethylamino)benzyl]sulfanyl]propionic acid	C₁₂H₁₈N₂O₂S	详情	详情
(VI)	35379	(2S)-3-(benzoylsulfanyl)-2-methylpropionic acid	C₁₁H₁₂O₃S	详情	详情
(VII)	41584	S-[(2R)-3-chloro-2-methyl-3-oxopropyl] benzenecarbothioate	C₁₁H₁₁ClO₂S	详情	详情
(VIII)	35380	4-nitrophenyl (2S)-3-(benzoylsulfanyl)-2-methylpropanoate	C₁₇H₁₅NO₅S	详情	详情
(IX)	41583	(2R)-2-[[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]amino]-3-[[4-(dimethylamino)benzyl]sulfanyl]propionic acid	C₂₃H₂₈N₂O₄S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The esterification of 3-(benzoylsulfanyl)-2(S)-methylpropionic acid with 4-nitrophenol (II) by means of DCC in dichloromethane gives the corresponding ester (III), which is condensed with S-(4-cyclohexylbenzyl)-L-cysteine (IV) (obtained by alkylation of L-cysteine (V) with 4-cyclohexylbenzyl bromide (VI)) to yield the corresponding amide (VII). Finally, this compound is debenzoylated by a treatment with aqueous NH4OH.

参考文献中间体

合成目标

【1】 Horiuchi, M.; Fujimura, K.; Suhara, H. (Santen Pharmaceutical Co., Ltd.); Novel sulfur-containing amino acid derivs.. EP 0947502; JP 1998130225; US 6046235; WO 9809943 .

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)	35379	(2S)-3-(benzoylsulfanyl)-2-methylpropionic acid		C₁₁H₁₂O₃S	详情	详情
(II)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(III)	35380	4-nitrophenyl (2S)-3-(benzoylsulfanyl)-2-methylpropanoate		C₁₇H₁₅NO₅S	详情	详情
(IV)	35381	(2R)-2-amino-3-[(4-cyclohexylbenzyl)sulfanyl]propionic acid		C₁₆H₂₃NO₂S	详情	详情
(V)	14643	L-cysteine; (R)-2-Amino-3-mercaptopropionic acid	52-90-4	C₃H₇NO₂S	详情	详情
(VI)	35382	1-(bromomethyl)-4-cyclohexylbenzene		C₁₃H₁₇Br	详情	详情
(VII)	35383	(2R)-2-[[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]amino]-3-[(4-cyclohexylbenzyl)sulfanyl]propionic acid		C₂₇H₃₃NO₄S₂	详情	详情

Extended Information