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【结 构 式】

【分子编号】56269

【品名】(2R,4S)-1-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-2-benzyl-4-hydroxy-5-iodo-1-pentanone

【CA登记号】

【 分 子 式 】C24H28INO4

【 分 子 量 】521.39513

【元素组成】C 55.29% H 5.41% I 24.34% N 2.69% O 12.27%

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:(XXIV)

Bromochromanone (XVI) was prepared by bromination of 4-chromanone (XV). Subsequent reduction of (XVI) with NaBH4 provided bromohydrin (XVII). Ritter reaction of (XVII) with acetonitrile and sulfuric acid, followed by acidic hydrolysis, led to racemic cis-3-bromo-4-chromanol, which was then resolved by means of (S)-(+)-mandelic acid. The desired (S,S)-isomer (XVIII) was coupled with hydrocinnamic acid (XIX) giving amide (XX). After protection of hydroxy amide (XX) as the acetonide (XXI), the lithium enolate of amide (XXI) was alkylated with allyl bromide (XXII) to furnish the (S)-2-benzyl-4-pentenamide (XXIII) as the main diastereoisomer. Halogenation of (XXIII) with N-iodosuccinimide in H2O-EtOAc afforded iodohydrin (XXIV), which was cyclized to epoxide (XXV) in the presence of NaOMe.

1 gamma-Hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides as HIV protease inhibitors. EP 1242426; WO 0138332 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XV) 14461 2,3-Dihydro-4H-chromen-4-one; 4-Chromanone 491-37-2 C9H8O2 详情 详情
(XVI) 56263 3-bromo-2,3-dihydro-4H-chromen-4-one C9H7BrO2 详情 详情
(XVII) 56264 3-bromo-4-chromanol C9H9BrO2 详情 详情
(XVIII) 56265 (3S,4S)-4-amino-3,4-dihydro-2H-chromen-3-ol C9H11NO2 详情 详情
(XIX) 49181 Hydrocinnamic acid; 3-Phenylpropionic acid; Benzylacetic acid 501-52-0 C9H10O2 详情 详情
(XX) 56266 N-[(3S,4S)-3-hydroxy-3,4-dihydro-2H-chromen-4-yl]-3-phenylpropanamide C18H19NO3 详情 详情
(XXI) 56267 1-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-3-phenyl-1-propanone C21H23NO3 详情 详情
(XXII) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(XXIII) 56268 (2S)-1-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-2-benzyl-4-penten-1-one C24H27NO3 详情 详情
(XXIV) 56269 (2R,4S)-1-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-2-benzyl-4-hydroxy-5-iodo-1-pentanone C24H28INO4 详情 详情
(XXV) 56270 (2R)-1-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-2-benzyl-3-[(2S)oxiranyl]-1-propanone C24H27NO4 详情 详情
Extended Information