(S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone

Base Information

• Chemical Name: (S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone
• CAS No.: 71405-01-1
• Molecular Formula: C₈H₁₄N₂O₄
• Molecular Weight: 202.21
• DSSTox Substance ID: DTXSID50503692
• Nikkaji Number: J2.684.496G
• Wikidata: Q82357692
• Mol file: 71405-01-1.mol

Synonyms:71405-01-1;(S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone;TERT-BUTYL N-[(3S)-1-HYDROXY-2-OXOAZETIDIN-3-YL]CARBAMATE;tert-Butyl (S)-(1-hydroxy-2-oxoazetidin-3-yl)carbamate;(S)-(1-Hydroxy-2-oxo-3-azetidinyl)carbamic Acid 1,1-Dimethylethyl Ester;SCHEMBL11000066;DTXSID50503692;CS-0058926;D73088;tert-Butyl(S)-(1-hydroxy-2-oxoazetidin-3-yl)carbamate;tert-Butyl [(3S)-1-hydroxy-2-oxoazetidin-3-yl]carbamate

Chemical Property of (S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone

Chemical Property:

• Refractive Index: 1.529
• PSA: 78.87000
• Density: 1.297g/cm³
• LogP: 0.43990
• Solubility.: Chloroform, Dichloromethane, Methanol
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 202.09535693
• Heavy Atom Count: 14
• Complexity: 259

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CN(C1=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1CN(C1=O)O

Technology Process of (S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone

There total 4 articles about (S)-3-(N-Boc-amino)-1-hydroxy-2-azetidinone 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: 100.0%

(2S)-N-(benzyloxy)-2-azetidinone (71405-00-0) → 3-<(tert-butoxycarbonyl)amino>-1-hydroxy-2-azetidinone (71405-01-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 0.75h; under 760 Torr;

DOI:10.1021/jo01291a007

Reference yield:

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → 3-<(tert-butoxycarbonyl)amino>-1-hydroxy-2-azetidinone (71405-01-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 79.5 percent / dicyclohexylcarbodiimide / tetrahydrofuran; H₂O / 3 h / pH 4.5

2: 62 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 6 h / 50 °C

3: 100 percent / H₂ / 10percent Pd/C / methanol / 0.75 h / 760 Torr

With hydrogen; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo01291a007

Reference yield:

L-tert-butyl {1-[(benzyloxy)amino]-3-hydroxy-1-oxopropan-2-yl}carbamate (26048-92-0) → 3-<(tert-butoxycarbonyl)amino>-1-hydroxy-2-azetidinone (71405-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 6 h / 50 °C

2: 100 percent / H₂ / 10percent Pd/C / methanol / 0.75 h / 760 Torr

With hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jo01291a007

upstream raw materials:

(2S)-N-(benzyloxy)-2-azetidinone

(S)-N-(tert-butoxycarbonyl)serine

L-tert-butyl {1-[(benzyloxy)amino]-3-hydroxy-1-oxopropan-2-yl}carbamate

Downstream raw materials:

C₂₄H₃₂N₂O₉

C₂₁H₃₂N₂O₈

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