5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

Base Information

Chemical Name:5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester
CAS No.:1184301-85-6
Molecular Formula:C₁₆H₂₃NO₄
Molecular Weight:293.363
Hs Code.:

Synonyms:5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

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Chemical Property of 5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

Chemical Property:

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Technology Process of 5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

There total 5 articles about 5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester 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: 83.0%

: 1184301-84-5
methyl 5-(((tert-butoxycarbonyl)amino)methyl)-2-methylbenzoate

: 74-88-4
methyl iodide

: 1184301-85-6
5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

Guidance literature:: methyl 5-(((tert-butoxycarbonyl)amino)methyl)-2-methylbenzoate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

methyl iodide; In tetrahydrofuran; toluene; at 0 - 23 ℃; Inert atmosphere;
DOI:10.1021/jm900611t

Reference yield:

: 1975-52-6
5-nitro-o-toluic acid

: 1184301-85-6
5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: thionyl chloride / 0 °C / Reflux

2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 23 °C

3.1: hydrogenchloride; sodium nitrite / water / 0 - 23 °C / Cooling with ice

4.1: sodium tetrahydroborate; methanol; nickel(II) chloride hexahydrate / 0 - 23 °C

4.2: 0.25 h

5.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 16 h / 0 - 23 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; thionyl chloride; nickel(II) chloride hexahydrate; hydrogen; potassium hexamethylsilazane; sodium nitrite; palladium 10% on activated carbon; In tetrahydrofuran; water; ethyl acetate; toluene;

Reference yield:

: 77324-87-9
methyl 2-methyl-5-nitrobenzoate

: 1184301-85-6
5-(N-tert-butoxycarbonylmethyl)methylamino-2-methylbenzoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 23 °C

2.1: hydrogenchloride; sodium nitrite / water / 0 - 23 °C / Cooling with ice

3.1: sodium tetrahydroborate; methanol; nickel(II) chloride hexahydrate / 0 - 23 °C

3.2: 0.25 h

4.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4.2: 16 h / 0 - 23 °C

With hydrogenchloride; methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen; potassium hexamethylsilazane; sodium nitrite; palladium 10% on activated carbon; In tetrahydrofuran; water; ethyl acetate; toluene;