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【结 构 式】

【分子编号】44117

【品名】methyl (2R)-2-[(1R)-1-hydroxybutyl]-4-methyl-4-pentenoate

【CA登记号】

【 分 子 式 】C11H20O3

【 分 子 量 】200.278

【元素组成】C 65.97% H 10.07% O 23.97%

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)

Hydrogenation of methyl butyrylacetate (I) in the presence of the chiral catalyst [RuCl2(BINAP)]2.Et3N furnished the (R)-hydroxyester (II). Alkylation of (II) with 3-bromo-2-methyl-1-propene (III) in the presence of lithium diisopropylamide gave the isobutenyl derivative (IV), which was further hydrogenated to (V) in the presence of Pd/C. After basic hydrolysis of the methyl ester of (V), the resulting carboxylic acid (VI) was coupled with 2-tetrahydropyranyloxyamine by means of EDC to provide the tetrahydropyranyl-protected hydroxamic acid (VII). Mesylation of the free hydroxyl group of (VII) to give (VIII), followed by its cyclization in the presence of potassium carbonate, gave rise to the azetidinone (IX). Opening of the lactam ring of (IX) with NaOH afforded the protected hydroxyamino acid (X). Then, formylation of the amino group with formic acetic anhydride in pyridine provided intermediate (XI).

1 Wiethe, R.W.; Andrews, R.C.; Rabinowitz, M.H.; Musso, D.L.; Chan, J.H.; McDougald, D.L.; Gaul, M.D.; Cowan, D.J.; Stanford, J.B.; Babacz, D.G.; Andersen, M.W. (Glaxo Group Ltd.); Formamide cpds. as therapeutic agents. US 6191150; WO 0012466 .
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) 44115 methyl 3-oxohexanoate 30414-54-1 C7H12O3 详情 详情
(II) 44116 methyl (3R)-3-hydroxyhexanoate C7H14O3 详情 详情
(III) 40015 3-bromo-2-methyl-1-propene 1458-98-6 C4H7Br 详情 详情
(IV) 44117 methyl (2R)-2-[(1R)-1-hydroxybutyl]-4-methyl-4-pentenoate C11H20O3 详情 详情
(V) 44118 methyl (2R,3R)-3-hydroxy-2-isobutylhexanoate C11H22O3 详情 详情
(VI) 44119 (2R,3R)-3-hydroxy-2-isobutylhexanoic acid C10H20O3 详情 详情
(VII) 44120 (2R,3R)-3-hydroxy-2-isobutyl-N-(tetrahydro-2H-pyran-2-yloxy)hexanamide C15H29NO4 详情 详情
(VIII) 44121 (1R,2R)-4-methyl-1-propyl-2-[[(tetrahydro-2H-pyran-2-yloxy)amino]carbonyl]pentyl methanesulfonate C16H31NO6S 详情 详情
(IX) 44122 (3R,4S)-3-isobutyl-4-propyl-1-(tetrahydro-2H-pyran-2-yloxy)-2-azetidinone C15H27NO3 详情 详情
(X) 44123 (2R,3S)-2-isobutyl-3-[(tetrahydro-2H-pyran-2-yloxy)amino]hexanoic acid C15H29NO4 详情 详情
(XI) 44124 (2R,3S)-3-[formyl(tetrahydro-2H-pyran-2-yloxy)amino]-2-isobutylhexanoic acid C16H29NO5 详情 详情
Extended Information