dimethyl(1,1,2-trimethylpropyl)silyl (3S)-2,2-dimethyl-3-thiomorpholinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】32892

【品名】dimethyl(1,1,2-trimethylpropyl)silyl (3S)-2,2-dimethyl-3-thiomorpholinecarboxylate

【CA登记号】

【分子式】C₁₅H₃₁NO₂SSi

【分子量】317.56818

【元素组成】C 56.73% H 9.84% N 4.41% O 10.08% S 10.1% Si 8.84%

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：(XII)

The silylation of D-penicillamine (I) with dimethylhexylsilyl chloride (Dmhs-Cl) and DBU gives the ester (XI), which is cyclized with 1,2-dichloroethane and DBU in DMF, yielding 2,2-dimethylthiomorpholine-3(S)-carboxylic acid dimethylhexylsilyl ester (XII). The sulfonation of (XII) with the sulfonyl chloride (VI) as before affords 2,2-dimethyl-4-[4-(4-pyridyloxy)phenylsulfonyl]thiomorpholine-3(S)-carboxylic acid dimethylhexylsilyl ester (XIII), which is desilylated in refluxing methanol to give the free acid (XIV) Finally, this compound is treated with oxalyl chloride and hydroxylamine in dichloromethane.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Prinomastat. Drugs Fut 2000, 25, 2, 150.
【2】 Zook, S.E.; Dagnino, R. Jr.; Deason, M.E.; Bender, S.L.; Melnick, M.J. (Agouron Pharmaceuticals, Inc.); Metalloproteinase inhibitors, pharmaceutical compsns. containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation. EP 0874830; JP 2000502330; WO 9720824 .

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)	12567	(2S)-2-Amino-3-methyl-3-sulfanylbutyric acid; Penicillamine; 3-Mercapto-L-valine	1113-41-3	C₅H₁₁NO₂S	详情	详情
(VI)	32887	4-(4-pyridinyloxy)benzenesulfonyl chloride		C₁₁H₈ClNO₃S	详情	详情
(XI)	32891	dimethyl(1,1,2-trimethylpropyl)silyl (2S)-2-amino-3-methyl-3-sulfanylbutanoate		C₁₃H₂₉NO₂SSi	详情	详情
(XII)	32892	dimethyl(1,1,2-trimethylpropyl)silyl (3S)-2,2-dimethyl-3-thiomorpholinecarboxylate		C₁₅H₃₁NO₂SSi	详情	详情
(XIII)	32893	dimethyl(1,1,2-trimethylpropyl)silyl (3S)-2,2-dimethyl-4-[[4-(4-pyridinyloxy)phenyl]sulfonyl]-3-thiomorpholinecarboxylate		C₂₆H₃₈N₂O₅S₂Si	详情	详情
(XIV)	32894	(3S)-2,2-dimethyl-4-[[4-(4-pyridinyloxy)phenyl]sulfonyl]-3-thiomorpholinecarboxylic acid		C₁₈H₂₀N₂O₅S₂	详情	详情

Extended Information