(S)-[1-(Benzyloxy)-2-oxo-3-azetidinyl]carbamic acid benzyl ester

Base Information

• Chemical Name: (S)-[1-(Benzyloxy)-2-oxo-3-azetidinyl]carbamic acid benzyl ester
• CAS No.: 71404-99-4
• Molecular Formula: C18H18N2O4
• Molecular Weight: 326.352
• DSSTox Substance ID: DTXSID00472288
• Wikidata: Q82301126
• Mol file: 71404-99-4.mol

Synonyms:71404-99-4;(S)-[1-(BENZYLOXY)-2-OXO-3-AZETIDINYL]CARBAMIC ACID BENZYL ESTER;benzyl N-[(3S)-2-oxo-1-phenylmethoxyazetidin-3-yl]carbamate;DTXSID00472288;AKOS030242701

Chemical Property of (S)-[1-(Benzyloxy)-2-oxo-3-azetidinyl]carbamic acid benzyl ester

Chemical Property:

• Melting Point: 89 - 93°C
• PSA: 67.87000
• LogP: 2.58420
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Chloroform, Dichloromethane, DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 326.12665706
• Heavy Atom Count: 24
• Complexity: 431

Purity/Quality:

97% ^*data from raw suppliers

(S)-[1-(Benzyloxy)-2-oxo-3-azetidinyl]carbamicAcidBenzylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(=O)N1OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1[C@@H](C(=O)N1OCC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

Technology Process of (S)-[1-(Benzyloxy)-2-oxo-3-azetidinyl]carbamic acid benzyl ester

There total 11 articles about (S)-[1-(Benzyloxy)-2-oxo-3-azetidinyl]carbamic acid benzyl 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: 87.0%

(S)-{2-[(phenylmethyloxy)amino]-1-(hydroxymethyl)-2-oxoethyl}carbamic acid phenylmethyl ester (26048-94-2) → (S)-[1-(phenylmethyloxy)-2-oxo-3-azetidinyl]carbamic acid phenylmethyl ester (71404-99-4,1246814-58-3)

Guidance literature:

With triethylamine; triphenylphosphine; In tetrachloromethane; acetonitrile; at 20 ℃; for 24h;

DOI:10.1002/ejoc.200400508

Reference yield: 86.0%

O-benzyl-N-CBZ-β-chloro-L-alanine hydroxamate (71605-41-9) → (S)-[1-(phenylmethyloxy)-2-oxo-3-azetidinyl]carbamic acid phenylmethyl ester (71404-99-4,1246814-58-3)

Guidance literature:

With sodium hydride; In dichloromethane; at 50 ℃; for 12h;

DOI:10.1021/ja00543a021

Reference yield:

N-benzyloxyamine (622-33-3) → (S)-[1-(phenylmethyloxy)-2-oxo-3-azetidinyl]carbamic acid phenylmethyl ester (71404-99-4,1246814-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DCC / acetonitrile / 0 - 20 °C

2: 87 percent / PPh₃; Et₃N / acetonitrile; CCl₄ / 24 h / 20 °C

With triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrachloromethane; acetonitrile;

DOI:10.1002/ejoc.200400508

upstream raw materials:

(S)-{2-[(phenylmethyloxy)amino]-1-(hydroxymethyl)-2-oxoethyl}carbamic acid phenylmethyl ester

O-benzyl-N-CBZ-β-chloro-L-alanine hydroxamate

N-benzyloxyamine

N-(benzyloxycarbonyl)-L-serine

Downstream raw materials:

(S)-3-[(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine

2-oxo-3-(Cbz-amino)-1-azetidinyl sulfate tetra n-butyl ammonium salt

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

(S)-3-[nitroso(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine

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