Nelfinavir Regeoisomer (Impurity D)

Base Information

Chemical Name:Nelfinavir Regeoisomer (Impurity D)
CAS No.:1025935-06-1
Molecular Formula:C₃₂H₄₅N₃O₄S
Molecular Weight:567.793
Hs Code.:
UNII:XR9F9UWP44

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

Suppliers and Price of Nelfinavir Regeoisomer (Impurity D)

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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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

: 108-98-5
thiophenol

: 159989-64-7
nelfinavir

: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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:

: 108-98-5
thiophenol

: 188936-07-4
(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

: 159989-64-7
nelfinavir

: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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

: 159989-64-7
nelfinavir

: 1025935-06-1
(3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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