(+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate

Base Information

• Chemical Name: (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate
• CAS No.: 259794-64-4
• Molecular Formula: C₁₉H₂₈N₂O₅S
• Molecular Weight: 396.508

Synonyms:(+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate

Chemical Property of (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate

Chemical Property:

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Technology Process of (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate

There total 8 articles about (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate 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: 65.0%

(+/-)-methyl 2-[({[2-(tert-butoxycarbonyl)-2,2-dimethylethyl]amino}sulfonyl)amino]-4-phenylbutanoate (259794-60-0) → (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]propanoate (259794-64-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 7h; Heating;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

Reference yield:

aminopivalic acid (19036-43-2) → (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]propanoate (259794-64-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / aq. NaOH / dioxane / 5 h / 20 °C

2: 85 percent / H₂SO₄ / CH₂Cl₂ / 65 h / 20 °C / sealed tube

3: 89 percent / H₂ / Pd/C / methanol / 3 h / 750.06 Torr

4: 64 percent / Et₃N / acetonitrile / 12 h / Heating

5: 65 percent / NaH / tetrahydrofuran / 7 h / Heating

With sodium hydroxide; sulfuric acid; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile; 1: Condensation / 2: Addition / 3: Hydrogenolysis / 4: Substitution / 5: Cyclization;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

Reference yield:

Methyl 2,2-dimethyl-3-hydroxypropionate (14002-80-3) → (+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]propanoate (259794-64-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 77 percent / PPh₃; DEAD / tetrahydrofuran / 20 h / 20 °C

2: 67 percent / aq. HCl / acetic acid / 16 h / Heating

3: 68 percent / aq. NaOH / dioxane / 5 h / 20 °C

4: 85 percent / H₂SO₄ / CH₂Cl₂ / 65 h / 20 °C / sealed tube

5: 89 percent / H₂ / Pd/C / methanol / 3 h / 750.06 Torr

6: 64 percent / Et₃N / acetonitrile / 12 h / Heating

7: 65 percent / NaH / tetrahydrofuran / 7 h / Heating

With hydrogenchloride; sodium hydroxide; sulfuric acid; hydrogen; sodium hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetic acid; acetonitrile; 1: Condensation / 2: Hydrolysis / 3: Condensation / 4: Addition / 5: Hydrogenolysis / 6: Substitution / 7: Cyclization;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

upstream raw materials:

(+/-)-methyl 2-[({[2-(tert-butoxycarbonyl)-2,2-dimethylethyl]amino}sulfonyl)amino]-4-phenylbutanoate

aminopivalic acid

Methyl 2,2-dimethyl-3-hydroxypropionate

3-(benzyloxycarbonylamino)-2,2-dimethylpropanoic acid

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