tert-butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate
• CAS No.: 171919-76-9
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.223
• European Community (EC) Number: 898-396-0
• Nikkaji Number: J669.254K

Synonyms:171919-76-9;tert-butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate;(S)-tert-Butyl 2-methyl-3-oxoazetidine-1-carboxylate;MFCD28501893;tert-butyl(2S)-2-methyl-3-oxoazetidine-1-carboxylate;(2S)-1-Boc-2-methyl-3-oxoazetidine;BS-43244;CID 15199114;CS-0077700;D84832;t-Butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate;tert-Butyl (S)-2-methyl-3-oxoazetidine-1-carboxylate

Chemical Property of tert-butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 242

Purity/Quality:

97% ^*data from raw suppliers

tert-butyl(2S)-2-methyl-3-oxoazetidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(=O)CN1C(=O)OC(C)(C)C
• Isomeric SMILES: C[C@H]1C(=O)CN1C(=O)OC(C)(C)C

Technology Process of tert-butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate

There total 2 articles about tert-butyl (2S)-2-methyl-3-oxoazetidine-1-carboxylate 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: 59.0%

(S)-3-[(tert-butoxy)carbonylamino]-1-diazobutan-2-one (67919-80-6) → tert-butyl (S)-2-methyl-3-oxoazetidine-1-carboxylate (171919-76-9,1638744-93-0)

Guidance literature:

With dirhodium tetraacetate; triethylamine; In dichloromethane; at 0 ℃; for 14h;

DOI:10.1002/hlca.19950780516

Reference yield:

L-N-Boc-Ala (15761-38-3) → tert-butyl (S)-2-methyl-3-oxoazetidine-1-carboxylate (171919-76-9,1638744-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / -15 - 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: dirhodium tetraacetate; triethylamine / dichloromethane / 0 °C / Inert atmosphere

With dirhodium tetraacetate; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol3016447

Reference yield: 74.0%

phenylmagnesium bromide (100-58-3) + tert-butyl (S)-2-methyl-3-oxoazetidine-1-carboxylate (171919-76-9,1638744-93-0) → tert-butyl (2S,3S)-3-hydroxy-2-methyl-3-phenylazetidine-1-carboxylate

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1002/hlca.19950780516

upstream raw materials:

(S)-3-[(tert-butoxy)carbonylamino]-1-diazobutan-2-one

L-N-Boc-Ala

Downstream raw materials:

tert-butyl (2S,3S)-3-hydroxy-2-methylazetidine-1-carboxylate

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