benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate

Base Information

• Chemical Name: benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate
• CAS No.: 849358-12-9
• Molecular Formula: C₂₁H₂₈N₂O₇S
• Molecular Weight: 452.529

Synonyms:benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate

Chemical Property of benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate

Chemical Property:

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Technology Process of benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate

There total 2 articles about benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate 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: 40.0%

6β-(tert-butoxycarbonyl)aminopenicillanic acid sulfone benzyl ester (849358-19-6) + methyl iodide (74-88-4) → benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate (849358-12-9)

Guidance literature:

6β-(tert-butoxycarbonyl)aminopenicillanic acid sulfone benzyl ester; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.0833333h;

methyl iodide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1023/B:COHC.0000040782.42204.4f

Reference yield:

6β-(tert-butoxycarbonyl)aminopenicillanic acid benzyl ester (124870-89-9) → benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate (849358-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 69 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

2.1: DBU / CH₂Cl₂ / 0.08 h / 20 °C

2.2: 40 percent / CH₂Cl₂ / 1 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1023/B:COHC.0000040782.42204.4f

Reference yield: 20.0%

benzyl 2-[3-tert-butoxycarbonylamino-4(R)-(methylsulfonyl)-2-oxoazetidinyl-1]-2-(isopropyliden)acetate (849358-12-9) → benzyl 2-[3(R)-amino-4(R)-methylsulfonyl-2-oxoazetidinyl-1]-2-(isopropyliden)acetate + benzyl 2-[3(S)-amino-4(R)-methylsulfonyl-2-oxoazetidinyl-1]-2-(isopropyliden)acetate

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1023/B:COHC.0000040782.42204.4f

upstream raw materials:

6β-(tert-butoxycarbonyl)aminopenicillanic acid sulfone benzyl ester

methyl iodide

6β-(tert-butoxycarbonyl)aminopenicillanic acid benzyl ester

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