(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

Base Information

Chemical Name:(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate
CAS No.:327025-13-8
Molecular Formula:C₂₁H₃₁NO₆Si
Molecular Weight:421.566
Hs Code.:

Synonyms:(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

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

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Chemical Property of (2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

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Technology Process of (2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

There total 5 articles about (2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate 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: 60.0%

: 327025-12-7
(2S)-methyl-[2-acetamido-4-(2-iodo-3,4,5-trimethoxyphenyl)]butanoate

: 1066-54-2
trimethylsilylacetylene

: 327025-13-8
(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; In dimethyl sulfoxide; at 90 ℃; for 15h;
DOI:10.1016/S0040-4020(00)00862-0

Reference yield:

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 327025-13-8
(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: zinc-copper couple / benzene; N,N-dimethyl-acetamide / 3 h / 20 °C / sonication

1.2: 31 percent / bis(triphenylphosphine)palladium dichloride / benzene; N,N-dimethyl-acetamide / 2 h / sonication

2.1: 91 percent / H₂ / Pd/C / ethanol; H₂O / 22 h / 3102.89 Torr

3.1: 93 percent / NaHCO₃; silver trifluoroacetate; I₂ / CHCl₃ / 2 h / 0 °C

4.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C

5.1: 454 mg / 4-(dimethylamino)pyridine; Et₃N / diethyl ether / 10 h

6.1: 60 percent / Et₂NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; zinc copper; hydrogen; iodine; silver trifluoroacetate; sodium hydrogencarbonate; diethylamine; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; ethanol; chloroform; N,N-dimethyl acetamide; water; dimethyl sulfoxide; benzene; 6.1: Sonogashira coupling;
DOI:10.1016/S0040-4020(00)00862-0

Reference yield:

: 327025-09-2
(2S)-methyl-[2-tert-butoxycarbonylamino-4-oxo-4-(3,4,5-trimethoxyphenyl)]butanoate

: 327025-13-8
(2S)-methyl-[2-acetamido-4-(2-trimethylsilylethynyl-3,4,5-trimethoxyphenyl)]butanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / H₂ / Pd/C / ethanol; H₂O / 22 h / 3102.89 Torr

2: 93 percent / NaHCO₃; silver trifluoroacetate; I₂ / CHCl₃ / 2 h / 0 °C

3: trifluoroacetic acid / diethyl ether / 3 h / 20 °C

4: 454 mg / 4-(dimethylamino)pyridine; Et₃N / diethyl ether / 10 h

5: 60 percent / Et₂NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; hydrogen; iodine; silver trifluoroacetate; sodium hydrogencarbonate; diethylamine; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; ethanol; chloroform; water; dimethyl sulfoxide; 5: Sonogashira coupling;
DOI:10.1016/S0040-4020(00)00862-0