Nelfinavir Regeoisomer (Impurity D)

Base Information

• Chemical Name: Nelfinavir Regeoisomer (Impurity D)
• CAS No.: 1025935-06-1
• Molecular Formula: C₃₂H₄₅N₃O₄S
• Molecular Weight: 567.793
• UNII: XR9F9UWP44
• Mol file: 1025935-06-1.mol

Synonyms:XR9F9UWP44;Nelfinavir Regeoisomer (Impurity D);(3S,4aS,8aS)-N-tert-Butyl-2-((2S,3S)-3-hydroxy-2-(3-hydroxy-2-methylbenzoylamino)-4-(phenylthio)butyl)-decahydroisoquinoline-3-carboxamide;1025935-06-1;3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-((2S,3S)-3-hydroxy-2-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-, (3S,4aS,8aS)-;N-tert-Butyl-2-((2S,3S)-3-hydroxy-2-((3-hydroxy-2-methylbenzoyl)amino)-4-phenylsulfanylbutyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide, (3S,4aS,8aS)-;UNII-XR9F9UWP44

Chemical Property of Nelfinavir Regeoisomer (Impurity D)

Chemical Property:

• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 567.31307810
• Heavy Atom Count: 40
• Complexity: 830

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=CC=C1O)C(=O)NC(CN2CC3CCCCC3CC2C(=O)NC(C)(C)C)C(CSC4=CC=CC=C4)O
• Isomeric SMILES: CC1=C(C=CC=C1O)C(=O)N[C@@H](CN2C[C@H]3CCCC[C@H]3C[C@H]2C(=O)NC(C)(C)C)[C@@H](CSC4=CC=CC=C4)O

Technology Process of Nelfinavir Regeoisomer (Impurity D)

There total 9 articles about Nelfinavir Regeoisomer (Impurity D) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

(2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-4-hydroxybutan-2-yl-4-methoxybenzoate + thiophenol (108-98-5) → nelfinavir (159989-64-7) + (3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (1025935-06-1)

Guidance literature:

(2R,3S)-3-(3-acetoxy-2-methylbenzamido)-1-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-4-hydroxybutan-2-yl-4-methoxybenzoate; With methanesulfonyl chloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

thiophenol; at 120 ℃;

With potassium carbonate; In methanol; at 40 ℃;

DOI:10.1021/acs.joc.8b00039

Reference yield:

thiophenol (108-98-5) + (3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide (188936-07-4) → nelfinavir (159989-64-7) + (3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (1025935-06-1)

Guidance literature:

With potassium hydrogencarbonate; In various solvent(s); at 115 ℃; for 4h;

DOI:10.1021/jo981472n

Reference yield:

(3S,4aS,8aS)-N-tert-butyl-2-(((4S,5R)-2-(4-methoxyphenyl)-4-vinyl-4,5-dihydrooxazol-5-yl)methyl)decahydroisoquinoline-3-carboxamide → nelfinavir (159989-64-7) + (3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (1025935-06-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / tetrahydrofuran; water / 3.5 h / 20 °C

2.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

3.1: hydrogenchloride; ozone; oxygen / dichloromethane; ethyl acetate / 0.58 h / -78 °C

3.2: 3 h / -78 - 0 °C

4.1: triethylamine; methanesulfonyl chloride / N,N-dimethyl-formamide / 20 °C

4.2: 120 °C

4.3: 40 °C

With hydrogenchloride; oxygen; ozone; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.8b00039

upstream raw materials:

thiophenol

(3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide

Acetic acid 3-((5S,6R)-6-hydroxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester

Acetic acid 3-((5S,6R)-6-methanesulfonyloxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester