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Velpatasvir intermediate

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Velpatasvir intermediate Basic information

Product Name:
Velpatasvir intermediate
Synonyms:
  • (2S,4S)-2-[5-[1,11-Dihydro-2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4',3':6,7]naphth[1,2-d]imidazol-9-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl e
  • tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate (N-2 step)
  • intermediate for Velpatasvir
  • (2S,4S)-2-[5-[1,11-Dihydro-2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4',3':6,7]naphth[1,2-d]imidazol-9-yl]-1H-imidazol-2-yl]-4-(methoxym
  • (2S,4S)-TERT-BUTYL 2-(5-(2-((2S,5S)-1-((S)-2-((METHOXYCARBONYL)AMINO)-3-METHYLBUTANOYL)-5-METHYLPYRROLIDIN-2-YL)-1,11-DIHYDROISOCHROMENO[4',3':6,7]NAPHTHO[1,2-D]IMIDAZOL-9-YL)-1H-IMIDAZOL-2-YL)-4-(METHOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE
  • (2S,4S)-2-[5-[1,11-Dihydro-2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4
  • (2S,4S)-2-[5-[1,11-Dihydro-2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4',3':6,7]naphth[1,2-d]imidazol-9-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester
  • tert-butyl (2S,4S)-2-(5-(2-((2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methyl
CAS:
1378391-45-7
MF:
C44H53N7O7
MW:
791.93
EINECS:
807-100-0
Product Categories:
  • 1378391-45-7
Mol File:
1378391-45-7.mol
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Velpatasvir intermediate Chemical Properties

Boiling point:
1045.8±65.0 °C(Predicted)
Density 
1.275±0.06 g/cm3(Predicted)
pka
11.22±0.46(Predicted)
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Velpatasvir intermediate Usage And Synthesis

Uses

Velpatasvir S, R Isomer (Imidazole) BOC acts as a reagent in the preparation of peptide analog as antiviral agents, preparation of condensed pentacyclic imidazole derivatives as antiviral compounds.

Uses

Intermediates of Velpatasvir can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly for the synthesis of API Velpatasvir.

Synthesis


tot-Butyl (2S,4S)-2-[5-(2-{(2S,5S)-l-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}- l,ll-dihydroisochromeno[4',3':6,7]naphtho[l,2-d]imidazol-9-yl)-lH-imidazol-2-yl]-4- (methoxymethyl)pyrrolidine-l-carboxylate tert-Butyl (2S,4S)-2-[5-(2- {(2S,5S)-l-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2- yl} -l ,4,5,l l-tetrahydroisochromeno[4',3':6,7]naphtho[l,2-d]imidazol-9-yl)-lH-imidazol-2-yl]-4- (methoxymethyl)pyrrolidine-l-carboxylate (8.33 g, 1.049 mmol) was suspended in DCM and activated Mn02 (55.0 g, 630 mmol) was added in a single portion. After 13 h, MeOH (200 mL) was added and the slurry was filtered over celite. The filter cake was washed with MeOH (600 mL) and the filtrate was concentrated under reduced pressure. The crude material was purified by silica column chromatography (0% to 45% MeOH/EtOAc) to afford tert-butyl (2S,4S)-2-[5-(2- {(2S,5S)-l-[N- (methoxycarbonyl)-L-valyl] -5 -methylpyrrolidin-2-yl} -1,11- dihydroisochromeno[4',3':6,7]naphtho[l,2-d]imidazol-9-yl)-lH-imidazol-2-yl]-4- (methoxymethyl)pyrrolidine-l-carboxylate (4.85 g, 58%).

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