Triacetoxyperiodinane → Telaprevir

HRID 391494ノート

反応式

HRID 391494 の反応式
[CH:1]1([C@H:7]([NH:41][C:42]([C:44]2[CH:49]=[N:48][CH:47]=[CH:46][N:45]=2)=[O:43])[C:8]([NH:10][C@@H:11]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:12]([N:14]2[CH2:18][C@@H:17]3[CH2:19][CH2:20][CH2:21][C@@H:16]3[C@H:15]2[C:22]([NH:24][C@@H:25]([CH2:34][CH2:35][CH3:36])[CH:26]([OH:33])[C:27]([NH:29][CH:30]2[CH2:32][CH2:31]2)=[O:28])=[O:23])=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CC1(C)N([O])C(C)(C)CCC1.Cl[O-].[Na+].S(=O)(O)[O-].[Na+]>ClCCl>[CH:1]1([C@H:7]([NH:41][C:42]([C:44]2[CH:49]=[N:48][CH:47]=[CH:46][N:45]=2)=[O:43])[C:8]([NH:10][C@@H:11]([C:37]([CH3:38])([CH3:39])[CH3:40])[C:12]([N:14]2[CH2:18][C@@H:17]3[CH2:19][CH2:20][CH2:21][C@@H:16]3[C@H:15]2[C:22]([NH:24][C@@H:25]([CH2:34][CH2:35][CH3:36])[C:26](=[O:33])[C:27]([NH:29][CH:30]2[CH2:31][CH2:32]2)=[O:28])=[O:23])=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 5

HCID 159087Triacetoxyperiodinane2 回HCID 2724126TempoHCID 23634854Telaprevir, (alpha-ketoamide bond reduced)-2 回HCID 23665760Sodium HypochloriteHCID 23665763Sodium Bisulfite

生成物 1

HCID 3010818Telaprevir

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The title compound is prepared by oxidation of the product of Step h with a suitable oxidizing reagent such as Dess-Martin periodinane or TEMPO and sodium hypochlorite. Specifically, in a flask containing 1.31 g of (1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide in 40 mL of dichloromethane is added at room temperature 1.06 g of Dess-Martin periodinane. After 2 hours of stirring, 50 mL of sodium bisulfite (1N) is added, and the mixture is stirred for 30 minutes. The 2 phases are separated, the organic is washed with water twice, brine and dried over Na2SO4. The crude product was purified by chromatography on silica (ethyl acetate 20-100% in Hexanes) to give the title compound. The diastereoisome ratio is determined by chiral HPLC normal phase.

後処理

  1. stirringthe mixture is stirred for 30 minutes
  2. customThe 2 phases are separated
  3. washthe organic is washed with water twice
  4. dry with materialbrine and dried over Na2SO4
  5. customThe crude product was purified by chromatography on silica (ethyl acetate 20-100% in Hexanes)

出典と根拠

ORDレコード
ord-db32157f4c124b77bce2000049c4d30d
出典データセット
uspto-grants-2013_02
特許番号
US08383858B2

反応ノート

読み込み中…