Methyl-2-(tert-butoxycarbonylamino)-2-cyclopropylacetate

Base Information

• Chemical Name: Methyl-2-(tert-butoxycarbonylamino)-2-cyclopropylacetate
• CAS No.: 638207-62-2
• Molecular Formula: C11H19 N O4
• Molecular Weight: 229.276
• DSSTox Substance ID: DTXSID50461642
• Mol file: 638207-62-2.mol

Synonyms:638207-62-2;METHYL-2-(TERT-BUTOXYCARBONYLAMINO)-2-CYCLOPROPYLACETATE;Methyl 2-cyclopropyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate;SCHEMBL14831257;DTXSID50461642;MFCD27578452;SY322992;FT-0752848;Methyl (R)-2-(Boc-amino)-2-cyclopropylacetate;Methyl [(tert-butoxycarbonyl)amino](cyclopropyl)acetate;Methyl 2-(tert-Butoxycarbonylamino)-2-cyclopropylacetate

Chemical Property of Methyl-2-(tert-butoxycarbonylamino)-2-cyclopropylacetate

Chemical Property:

• Vapor Pressure: 0.000298mmHg at 25°C
• Melting Point: 49 °C
• Boiling Point: 321.4oC at 760 mmHg
• PKA: 11.13±0.46(Predicted)
• Flash Point: 148.2oC
• PSA: 68.12000
• Density: 1.125g/cm3
• LogP: 1.66710
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1CC1)C(=O)OC

Technology Process of Methyl-2-(tert-butoxycarbonylamino)-2-cyclopropylacetate

There total 5 articles about Methyl-2-(tert-butoxycarbonylamino)-2-cyclopropylacetate 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:

di-tert-butyl dicarbonate (24424-99-5) + methyl 2-amino-2-cyclopropylacetate (768356-83-8) → methyl 2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate (638207-62-2)

Guidance literature:

di-tert-butyl dicarbonate; methyl 2-amino-2-cyclopropylacetate; With hydroxylamine hydrochloride; potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 12h;

With 1-amino-3-(dimethylamino)propane; In 1,4-dioxane; water; at 20 ℃; for 1h;

DOI:10.1002/adsc.200606038

Reference yield:

methyl 2-(N-tert-butoxycarbonyl-N-chloroamino)-2-cyclopropylacetate (638207-64-4) → methyl 2-(N-tert-butoxycarbonylimino)-2-cyclopropylacetate (936097-38-0) + methyl 2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate (638207-62-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1002/adsc.200606038

Reference yield:

cyclopropyl-hydroxyiminoacetic acid (936097-37-9) → methyl 2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate (638207-62-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / Zn / acetic acid / 0.5 h / 20 - 30 °C

2.1: SOCl₂ / methanol / 20 h / 20 °C

3.1: K₂CO₃; NH₂OH*HCl / dioxane; H₂O / 12 h / 20 °C

3.2: 18.5 g / 3-dimethylaminopropylamine / dioxane; H₂O / 1 h / 20 °C

With thionyl chloride; hydroxylamine hydrochloride; potassium carbonate; zinc; In 1,4-dioxane; methanol; water; acetic acid;

DOI:10.1002/adsc.200606038

upstream raw materials:

di-tert-butyl dicarbonate

methyl 2-amino-2-cyclopropylacetate

methyl 2-(N-tert-butoxycarbonyl-N-chloroamino)-2-cyclopropylacetate

cyclopropyl-hydroxyiminoacetic acid

Downstream raw materials:

methyl (S)-2-(N-tert-butoxycarbonylamino)-2-cyclopropylacetate

(2S)-2-[[(tert-butoxy)carbonyl]amino]-2-cyclopropylacetic acid

tert-butyl 1-cyclopropyl-2-oxoethylcarbamate

(S)-2-amino-2-cyclopropylacetic acid

Refernces