3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Base Information

Chemical Name:3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester
CAS No.:258845-36-2
Molecular Formula:C₂₆H₃₇N₇O₇S
Molecular Weight:591.688
Hs Code.:

3-[(5-{2-[3-(1<i>H</i>-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid <i>tert</i>-butyl ester

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Chemical Property of 3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

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Technology Process of 3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

There total 12 articles about 3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl 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:

: 773-64-8
2-mesitylenesulphonyl chloride

: 258845-36-2
3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / Et₃N / tetrahydrofuran; H₂O / 3.5 h / 20 °C

2: 83 percent / aq. NaOH; Br₂ / 1 h / 85 °C

3: 63 percent / H₂SO₄ / dioxane / 114 h

4: N-methylmorpholine; BOP / dioxane / 18 h / 20 °C

5: Ph₃P; aq. NH₃ / dioxane

6: Et₃N / CH₂Cl₂; toluene / 3 h / 20 °C

7: CH₂Cl₂; toluene / 18 h

With 4-methyl-morpholine; ammonium hydroxide; sodium hydroxide; sulfuric acid; bromine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 1: sulfonylation / 2: Hoffmann's degradation / 3: Esterification / 4: Condensation / 5: Reduction / 6: Condensation / 7: Condensation;
DOI:10.1021/jm9900321

Reference yield:

: 258844-47-2
ethyl 5-(2-hydroxyethyl)-4,5-dihydro-3-isoxazolecarboxylate

: 258845-36-2
3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂ / 18 h / 20 °C

2: NaN₃ / dimethylformamide

3: aq. NaOH / ethanol / 2 h / 20 °C

4: N-methylmorpholine; BOP / dioxane / 18 h / 20 °C

5: Ph₃P; aq. NH₃ / dioxane

6: Et₃N / CH₂Cl₂; toluene / 3 h / 20 °C

7: CH₂Cl₂; toluene / 18 h

With 4-methyl-morpholine; pyridine; ammonium hydroxide; sodium hydroxide; sodium azide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; triphenylphosphine; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Tosylation / 2: Substitution / 3: Hydrolysis / 4: Condensation / 5: Reduction / 6: Condensation / 7: Condensation;
DOI:10.1021/jm9900321

Reference yield:

: 258844-49-4
5-(2-azido-ethyl)-4,5-dihydro-isoxazole-3-carboxylic acid

: 258845-36-2
3-[(5-{2-[3-(1H-imidazol-2-yl)-ureido]-ethyl}-4,5-dihydro-isoxazole-3-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: N-methylmorpholine; BOP / dioxane / 18 h / 20 °C

2: Ph₃P; aq. NH₃ / dioxane

3: Et₃N / CH₂Cl₂; toluene / 3 h / 20 °C

4: CH₂Cl₂; toluene / 18 h

With 4-methyl-morpholine; ammonium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; triphenylphosphine; In 1,4-dioxane; dichloromethane; toluene; 1: Condensation / 2: Reduction / 3: Condensation / 4: Condensation;
DOI:10.1021/jm9900321