methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate

Base Information

• Chemical Name: methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate
• CAS No.: 1263101-85-4
• Molecular Formula: C₃₂H₄₈F₃NO₅SSi
• Molecular Weight: 643.884

Synonyms:methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate

Chemical Property of methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate

There total 11 articles about methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-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: 29.0%

N-methoxy-N-methyl-1-(trifluoromethyl)cyclobutanecarboxamide (1211521-38-8) + methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate (1263101-57-0) → methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate (1263101-85-4)

Guidance literature:

methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-iodothiophene-2-carboxylate; With isopropylmagnesium chloride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 0.5h;

N-methoxy-N-methyl-1-(trifluoromethyl)cyclobutanecarboxamide; In tetrahydrofuran; dichloromethane; at 20 ℃;

DOI:10.1021/jm401420j

Reference yield:

trans-4-methylcyclohexanecarboxylic acid (934-67-8,4331-54-8,13064-83-0) → methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate (1263101-85-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: dichloromethane; N,N-dimethyl-formamide / 3 h / 0 - 20 °C

2.1: pyridine / toluene / 16 h / Reflux

3.1: hydrogenchloride / tetrahydrofuran / 12 h / 40 °C

4.1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / -25 °C

5.1: 1H-imidazole / dichloromethane / 10 h / 0 - 9 °C / Inert atmosphere

6.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C

6.2: 3 h / -78 °C

7.1: isopropylmagnesium chloride / dichloromethane; tetrahydrofuran / 0.5 h / -78 °C

7.2: 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; isopropylmagnesium chloride; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm401420j

Reference yield:

trans-4-methylcyclohexanecarbonyl chloride (55930-23-9) → methyl 3-((1r,4R)-N-((1r,4R)-4-(tert-butyldimethylsilyloxy)cyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate (1263101-85-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / toluene / 16 h / Reflux

2.1: hydrogenchloride / tetrahydrofuran / 12 h / 40 °C

3.1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / -25 °C

4.1: 1H-imidazole / dichloromethane / 10 h / 0 - 9 °C / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C

5.2: 3 h / -78 °C

6.1: isopropylmagnesium chloride / dichloromethane; tetrahydrofuran / 0.5 h / -78 °C

6.2: 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; isopropylmagnesium chloride; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene;

DOI:10.1021/jm401420j

upstream raw materials:

trans-4-methylcyclohexanecarboxylic acid

trans-4-methylcyclohexanecarbonyl chloride

(1-trifluoromethyl)cyclobutanecarboxylic acid

N-methoxy-N-methyl-1-(trifluoromethyl)cyclobutanecarboxamide

Downstream raw materials:

methyl 3-((1r,4R)-N-((1r,4R)-4-hydroxycyclohexyl)-4-methylcyclohexanecarboxamido)-5-(1-(trifluoromethyl)cyclobutanecarbonyl)thiophene-2-carboxylate

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