(1R,2S,5S)-Methyl 3-((S)-2-(3-(t-butyl)ureido)-3,3-diMethyl butanoyl)-6,6-diMethyl-3-azabicyclo [3.1.0]hexane-2-carboxylate

Base Information

• Chemical Name: (1R,2S,5S)-Methyl 3-((S)-2-(3-(t-butyl)ureido)-3,3-diMethyl butanoyl)-6,6-diMethyl-3-azabicyclo [3.1.0]hexane-2-carboxylate
• CAS No.: 394735-26-3
• Molecular Formula: C20H34N2O5
• Molecular Weight: 382.5
• Mol file: 394735-26-3.mol

Synonyms:boc-tert-Leu;

Chemical Property of (1R,2S,5S)-Methyl 3-((S)-2-(3-(t-butyl)ureido)-3,3-diMethyl butanoyl)-6,6-diMethyl-3-azabicyclo [3.1.0]hexane-2-carboxylate

Chemical Property:

• PSA: 84.94000
• LogP: 2.91060

Purity/Quality:

98%Min ^*data from raw suppliers

(1R,2S,5S)- METHYL ESTER-3-[(2S)-2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3,3-DIMETHYL-1-OXOBUTYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2S,5S)-Methyl 3-((S)-2-(3-(t-butyl)ureido)-3,3-diMethyl butanoyl)-6,6-diMethyl-3-azabicyclo [3.1.0]hexane-2-carboxylate

There total 10 articles about (1R,2S,5S)-Methyl 3-((S)-2-(3-(t-butyl)ureido)-3,3-diMethyl butanoyl)-6,6-diMethyl-3-azabicyclo [3.1.0]hexane-2-carboxylate 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: 89.0%

methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride + N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) → (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester (394735-26-3)

Guidance literature:

methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride; N-tert-butyloxycarbonyl-L-tert-leucine; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; acetonitrile; at 0 - 25 ℃; for 16h; Large scale;

With hydrogenchloride; In water; for 0.1h; pH=5; Temperature; Large scale;

Reference yield:

(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate methyl ester (672325-23-4,672325-96-1) + N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) → (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester (394735-26-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2008.12.111

Reference yield:

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one (134107-65-6) → (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester (394735-26-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BuLi / tetrahydrofuran

1.2: tetrahydrofuran / -78 - 20 °C

2.1: LiAlH₄ / tetrahydrofuran / Heating

3.1: H₂ / Pd/C

4.1: acetone / 3 h / -5 °C

5.1: toluene; methanol

6.1: HCl / dioxane

7.1: BOP; N-methylmorpholine / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 4.1: Jones oxidation;

DOI:10.1021/jm060325b

upstream raw materials:

N-tert-butyloxycarbonyl-L-tert-leucine

3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Downstream raw materials:

(1R,2S,5S)-N-{(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-N-(trifluoroacetyl)-L-valyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide

(1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide

(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

methyl (1R,2S,5S)-3-((S)-2-(3-(tert-butyl)-ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

Refernces

• 1、 -. "ANTIVIRAL COMPOUNDS CONTAINING NITRILE". Page/Page column 118-120; 122; 126; 127. . Retrieved 2021/12/30.
• 2、 Morgan, Adam J.,Nguyen, Sophia,Uttamsingh, Vinita,Bridson, Gary,Harbeson, Scott,Tung, Roger,Masse, Craig E.. "Design and synthesis of deuterated boceprevir analogs with enhanced pharmacokinetic properties". scheme or table. p. 613 - 624. Retrieved 2011/12/03.