(S)-tert-Butyl 2-benzyl-3-oxoazetidine-1-carboxylate

Base Information

Chemical Name:(S)-tert-Butyl 2-benzyl-3-oxoazetidine-1-carboxylate
CAS No.:171919-78-1
Molecular Formula:C₁₅H₁₉NO₃
Molecular Weight:261.321
Hs Code.:
DSSTox Substance ID:DTXSID401160342
Nikkaji Number:J3.091.059A

Synonyms:(S)-tert-Butyl 2-benzyl-3-oxoazetidine-1-carboxylate;171919-78-1;tert-butyl (2S)-2-benzyl-3-oxoazetidine-1-carboxylate;SCHEMBL24723803;TQR0137;BERNCZJWUMYWDH-LBPRGKRZSA-N;DTXSID401160342;(5)-tert-butyl 2-benzyl-3-oxoazetidine-1-carboxylate;1,1-Dimethylethyl (2S)-3-oxo-2-(phenylmethyl)-1-azetidinecarboxylate

Suppliers and Price of (S)-tert-Butyl 2-benzyl-3-oxoazetidine-1-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
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Total 1 raw suppliers

Chemical Property of (S)-tert-Butyl 2-benzyl-3-oxoazetidine-1-carboxylate

Chemical Property:

XLogP3:2.8
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:261.13649347
Heavy Atom Count:19
Complexity:353

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(C)(C)OC(=O)N1CC(=O)C1CC2=CC=CC=C2
Isomeric SMILES:CC(C)(C)OC(=O)N1CC(=O)[C@@H]1CC2=CC=CC=C2

Technology Process of (S)-tert-Butyl 2-benzyl-3-oxoazetidine-1-carboxylate

There total 3 articles about (S)-tert-Butyl 2-benzyl-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: 63.0%

: 60398-41-6
(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate

: 171919-78-1
tert-butyl (S)-2-benzyl-3-oxoazetidine-1-carboxylate

Guidance literature:: With dirhodium tetraacetate; triethylamine; In dichloromethane; at 0 ℃; for 14h;
DOI:10.1002/hlca.19950780516

Reference yield:

: C₁₄H₂₅N₃O₃

: 100-39-0
benzyl bromide

: C₁₅H₁₉NO₃

: 171919-78-1
tert-butyl (S)-2-benzyl-3-oxoazetidine-1-carboxylate

Guidance literature:: C₁₄H₂₅N₃O₃; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 20h; Inert atmosphere;

With water; oxalic acid; In diethyl ether; at 20 ℃; for 20h; Overall yield = 57 %; Overall yield = 60 mg; stereoselective reaction; Saturated solution;
DOI:10.1021/acs.joc.6b01284

Reference yield:

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: C₁₅H₁₉NO₃

: 171919-78-1
tert-butyl (S)-2-benzyl-3-oxoazetidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 16 h / 55 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.2: 20 h / -78 - 20 °C / Inert atmosphere

2.3: 20 h / 20 °C / Saturated solution

With n-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1021/acs.joc.6b01284