Triacetoxyperiodinane → Telaprevir

HRID 391494노트

반응식

HRID 391494 반응식
[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

참가 물질

7

반응물 5

HCID 159087Triacetoxyperiodinane2회HCID 2724126TempoHCID 23634854Telaprevir, (alpha-ketoamide bond reduced)-2회HCID 23665760Sodium HypochloriteHCID 23665763Sodium Bisulfite

생성물 1

HCID 3010818Telaprevir

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-db32157f4c124b77bce2000049c4d30d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383858B2

반응 노트

불러오는 중…