Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-oxocyclobutane-1-carboxylate

Base Information

• Chemical Name: Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-oxocyclobutane-1-carboxylate
• CAS No.: 129287-91-8
• Molecular Formula: C₁₂H₁₉NO₅
• Molecular Weight: 257.287
• European Community (EC) Number: 959-372-6
• Mol file: 129287-91-8.mol

Synonyms:129287-91-8;ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-oxocyclobutane-1-carboxylate;Ethyl 1-((tert-butoxycarbonyl)amino)-3-oxocyclobutanecarboxylate;Ethyl 1-([(tert-butoxy)carbonyl]amino)-3-oxocyclobutane-1-carboxylate;Ethyl 1-(tert-butoxycarbonylamino)-3-oxo-cyclobutanecarboxylate;MFCD18633152;ethyl 1-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxocyclobutane-1-carboxylate;Cyclobutanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-3-oxo-, ethyl ester;Ethyl 1-Boc-amino-3-oxocyclobutane-1-carboxylate;SCHEMBL16112133;AMY32152;AKOS015900969;SB22124;AS-51328;SY099684;CS-0049558;P12420;Ethyl 1-(Boc-amino)-3-oxocyclobutanecarboxylate;A888871;Ethyl1-((tert-butoxycarbonyl)amino)-3-oxocyclobutanecarboxylate

Chemical Property of Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-oxocyclobutane-1-carboxylate

Chemical Property:

• Melting Point: 81-82℃
• Boiling Point: 369.1±42.0 °C(Predicted)
• PKA: 8.88±0.20(Predicted)
• PSA: 85.19000
• Density: 1.16
• LogP: 1.38030
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 257.12632271
• Heavy Atom Count: 18
• Complexity: 361

Purity/Quality:

97% ^*data from raw suppliers

Ethyl1-([(tert-Butoxy)carbonyl]amino)-3-oxocyclobutane-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC(=O)C1)NC(=O)OC(C)(C)C

Technology Process of Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-oxocyclobutane-1-carboxylate

There total 4 articles about Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-oxocyclobutane-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: 80.0%

ethyl 1-<<(tert-butyloxy)carbonyl>amino>-3-hydroxycyclobutane-1-carboxylate (413597-67-8) → ethyl 1-<<(tert-butyloxy)carbonyl>amino>-3-oxocyclobutane-1-carboxylate (129287-91-8)

Guidance literature:

With sodium periodate; ruthenium tetroxide; In tetrachloromethane; water;

DOI:10.1021/jm00172a036

Reference yield:

diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate (54166-15-3) → ethyl 1-<<(tert-butyloxy)carbonyl>amino>-3-oxocyclobutane-1-carboxylate (129287-91-8)

Guidance literature:

Multi-step reaction with 4 steps

1: KOH / ethanol

2: DPPA; Et₃N

3: H₂ / Pd/C / ethanol / 760.05 Torr

4: NaIO₄; RuO₂ / CCl₄

With ruthenium(IV) oxide; potassium hydroxide; sodium periodate; diphenyl-phosphinic acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrachloromethane; ethanol; 1: Hydrolysis / 2: Curtius rearrangement / 3: Hydrogenolysis / 4: Oxidation;

DOI:10.1021/jo000152c

Reference yield:

3-(benzyloxy)-1-carbethoxycyclobutane-1-carboxylic acid (180205-43-0) → ethyl 1-<<(tert-butyloxy)carbonyl>amino>-3-oxocyclobutane-1-carboxylate (129287-91-8)

Guidance literature:

Multi-step reaction with 3 steps

1: DPPA; Et₃N

2: H₂ / Pd/C / ethanol / 760.05 Torr

3: NaIO₄; RuO₂ / CCl₄

With ruthenium(IV) oxide; sodium periodate; diphenyl-phosphinic acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrachloromethane; ethanol; 1: Curtius rearrangement / 2: Hydrogenolysis / 3: Oxidation;

DOI:10.1021/jo000152c

upstream raw materials:

ethyl 1-<<(tert-butyloxy)carbonyl>amino>-3-hydroxycyclobutane-1-carboxylate

diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate

3-(benzyloxy)-1-carbethoxycyclobutane-1-carboxylic acid

ethyl 3-(benzyloxy)-1-<<(tert-butyloxy)carbonyl>amino>cyclobutane-1-carboxylate

Downstream raw materials:

tert-butyl N-[3,3-difluoro-1-(hydroxymethyl)cyclobutyl]carbamate

ethyl 1-<<(tert-butyloxy)carbonyl>amino>-3-hydroxycyclobutane-1-carboxylate

(E)-ethyl 1-<(tert-butoxycarbonyl)amino>-3-cyclobutane-1-carboxylate

(Z)-ethyl 1-<(tert-butoxycarbonyl)amino>-3-cyclobutane-1-carboxylate