3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid

Base Information

Chemical Name:3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid
CAS No.:1237536-05-8
Molecular Formula:C₁₅H₁₈F₃NO₅
Molecular Weight:349.307
Hs Code.:

Synonyms:3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid

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Chemical Property of 3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid

Chemical Property:

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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. 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: 46.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1237536-04-7
tert-butyl 3-((1S)-1-amino-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-(trifluoromethyl)benzoate

: 1237536-05-8
3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid

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

Reference yield:

: 328-67-6
3-bromo-5-(trifluoromethyl)benzoic acid

: 1237536-05-8
3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid

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

Reference yield:

: 1237535-81-7
tert-butyl 3-bromo-5-(trifluoromethyl)benzoate

: 1237536-05-8
3-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-5-(trifluoromethyl)benzoic acid

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