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Boceprevir InterMediates

Boceprevir InterMediates structure

CAS No:
565456-77-1
Formula:
C9H16ClNO2
Chemical Name:
Boceprevir InterMediates
Synonyms:
(1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride;Boceprevir InterMediates;Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, (Hydrochloride), (1R,2S,5S)- (9CI);(1S,2S,5R)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, hydrochloride, (1R,2S,5S)-;Methyl (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Boceprevir (Victrelis) is an orally administered ketoamide peptidomimetic inhibitor of the NS3 protease of HCV. Boceprevir InterMediates is an important intermediates in the synthesis process.

Boceprevir is a peptidomimetic protease inhibitor with four moieties, P1–P3 and a Cap, where P1 is a racemic β-aminoamide, P2 is a chiral dimethylcyclopropylproline analog, P3 is (S)-tert-leucine, and Cap is a tert-butylcarbamoyl group. The 3-azabicyclo[3.1.0]hexane structure of P2 adopts a constrained conformation, so that the gem-dimethyl group has a fixed angle with respect to the bicyclic ring structure. The incorporation of the 3-azabicyclo[3.1.0]hexane moiety results in a 1000-fold increase in NS3 protease binding over proline in a pentapeptide scaffold. When boceprevir binds to the NS3 protease, the P2 moiety interacts with four amino acid residues at the active site. The starting material for the P2 moiety is the HCl salt of the dimethylcyclopropylproline methyl ester 2. For medicinal chemistry studies, it was prepared by cyclopropanation of a Δ3-pyrroline derivative of pyroglutamic acid.

Boceprevir InterMediates Basic Attributes

Molecular Weight：

205.68

Exact Mass：

169.110278721

EC Number：

611-400-5

DSSTox ID：

DTXSID30459426

Color/Form：

Pale yellow

HScode：

2933998090

Characteristics

Critical Temperature & Pressure：

Inert atmosphere,Room Temperature

Boceprevir InterMediates Use and Manufacturing

(1R, 2S, 5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate methyl ester hydrochloride is the cost in the side chain synthesis of boceprevir the highest key intermediate.

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