Technology Process of (4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester
There total 5 articles about (4R,5S)-5-azido-4-(4-methoxyphenyl)-6-oxo-6-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]hexanoic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sodium azide;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 4h;
DOI:10.1021/jo0340152
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: oxalyl chloride; DMSO / CH2Cl2 / 0.25 h / -75 °C
2.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C
3.1: CuBr*Me2S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C
3.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C
3.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C
4.1: 850 mg / NaN3 / dimethylformamide / 4 h / 20 °C
With
sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
1.1: Swern oxidation / 3.2: Michael addition;
DOI:10.1021/jo0340152
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 74 percent / BH3*Me2S / tetrahydrofuran / 24 h / 20 °C
2.1: oxalyl chloride; DMSO / CH2Cl2 / 0.25 h / -75 °C
3.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C
4.1: CuBr*Me2S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C
4.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C
4.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C
5.1: 850 mg / NaN3 / dimethylformamide / 4 h / 20 °C
With
sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
2.1: Swern oxidation / 4.2: Michael addition;
DOI:10.1021/jo0340152
