Technology Process of 3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid
There total 5 articles about 3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
tert-butyl 3-((1S)-1-amino-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-(trifluoromethyl)benzoate;
With
trifluoroacetic acid;
In
dichloromethane;
at 20 ℃;
With
hydrogenchloride;
In
dichloromethane;
di-tert-butyl dicarbonate;
With
sodium hydroxide;
In
1,4-dioxane; water;
at 20 ℃;
for 3h;
DOI:10.1016/j.bmcl.2016.01.049
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 18 h / 20 °C
1.2: 1 h / 0 °C
2.1: palladium dichloride; triphenylphosphine; caesium carbonate / tetrahydrofuran; water / 85 °C
3.1: hydroquinine 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 20 °C
3.2: 4 h / 20 °C
4.1: triphenylphosphine; diphenyl phosphoryl azide; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 °C
4.2: 3 h / 60 °C
5.1: trifluoroacetic acid / dichloromethane / 20 °C
5.3: 3 h / 20 °C
With
oxalyl dichloride; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; hydroquinine 1,4-phthalazinediyl diether; caesium carbonate; triphenylphosphine; trifluoroacetic acid; palladium dichloride;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
2.1: |Suzuki Coupling / 3.1: |Sharpless Dihydroxylation / 4.1: |Mitsunobu Displacement / 4.2: |Mitsunobu Displacement;
DOI:10.1016/j.bmcl.2016.01.049
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: palladium dichloride; triphenylphosphine; caesium carbonate / tetrahydrofuran; water / 85 °C
2.1: hydroquinine 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 20 °C
2.2: 4 h / 20 °C
3.1: triphenylphosphine; diphenyl phosphoryl azide; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 °C
3.2: 3 h / 60 °C
4.1: trifluoroacetic acid / dichloromethane / 20 °C
4.3: 3 h / 20 °C
With
di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; hydroquinine 1,4-phthalazinediyl diether; caesium carbonate; triphenylphosphine; trifluoroacetic acid; palladium dichloride;
In
tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
1.1: |Suzuki Coupling / 2.1: |Sharpless Dihydroxylation / 3.1: |Mitsunobu Displacement / 3.2: |Mitsunobu Displacement;
DOI:10.1016/j.bmcl.2016.01.049