(5-benzyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester

Base Information

• Chemical Name: (5-benzyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester
• CAS No.: 603132-93-0
• Molecular Formula: C₁₅H₂₂N₂O₄S
• Molecular Weight: 326.417

Synonyms:(5-benzyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester

Chemical Property of (5-benzyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of (5-benzyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester

There total 4 articles about (5-benzyl-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidin-2-yl)-acetic 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: 76.0%

bromoacetic acid tert-butyl ester (5292-43-3) + 2-benzyl-1,2,5-thiadiazolidine 1,1-dioxide (144432-72-4) → (5-benzyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester (603132-93-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(03)00982-7

Reference yield:

N1-BOC-N3-benzylsulfamide (147000-78-0) → (5-benzyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester (603132-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 3 h / 20 °C

2: 80 percent / Bu₄NI; K₂CO₃ / acetone / 18 h / Heating

3: 90 percent / CF₃CO₂H / CH₂Cl₂ / 20 °C

4: 76 percent / DBU / tetrahydrofuran / 4 h / 20 °C

With di-isopropyl azodicarboxylate; tetra-(n-butyl)ammonium iodide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetone; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(03)00982-7

Reference yield:

N2-BOC-N5-benzyl-1,2,5-thiadiazolidine 1,1-dioxide (263719-86-4) → (5-benzyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-yl)-acetic acid tert-butyl ester (603132-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CF₃CO₂H / CH₂Cl₂ / 20 °C

2: 76 percent / DBU / tetrahydrofuran / 4 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(03)00982-7

upstream raw materials:

bromoacetic acid tert-butyl ester

2-benzyl-1,2,5-thiadiazolidine 1,1-dioxide

N¹-BOC-N³-benzylsulfamide

N²-BOC-N⁵-benzyl-1,2,5-thiadiazolidine 1,1-dioxide

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