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HRID391494

反应详情

EQUATION

反应方程式

HRID 391494 的结构方程式

REACTANTS

反应物

5
结构：CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21
HCID159087

Triacetoxyperiodinane

C13H13IO8

2 次

结构：CC1(C)CCCC(C)(C)N1[O]
HCID2724126

1-Piperidinyloxy, 2,2,6,6-tetramethyl-

C9H18NO

结构：CCC[C@H](NC(=O)[C@@H]1[C@H]2CCC[C@H]2CN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1cnccn1)C1CCCCC1)C(C)(C)C)C(O)C(=O)NC1CC1
HCID23634854

未命名化合物

2 次

结构：[Na+].[O-]Cl
HCID23665760

Sodium Hypochlorite

ClNaO

结构：O=S([O-])O.[Na+]
HCID23665763

Sodium Bisulfite

HNaO3S

PRODUCTS

生成物

1
结构：CCC[C@H](NC(=O)[C@@H]1[C@H]2CCC[C@H]2CN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1cnccn1)C1CCCCC1)C(C)(C)C)C(=O)C(=O)NC1CC1
HCID3010818

Telaprevir

C36H53N7O6

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

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.

WORKUP

后处理

  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)