(1R,2S)-Methyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate

Base Information

• Chemical Name: (1R,2S)-Methyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate
• CAS No.: 159622-09-0
• Molecular Formula: C12H19 N O4
• Molecular Weight: 241.287
• Hs Code.: 2902190000
• DSSTox Substance ID: DTXSID20439656
• Nikkaji Number: J1.802.358J
• Wikidata: Q82255673
• Mol file: 159622-09-0.mol

Synonyms:159622-09-0;(1R,2S)-Methyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate;(1R,2S)-1-tert-Butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester;Cyclopropanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-, methyl ester, (1R,2S)-;methyl (1R,2S)-2-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate;(1R,2S)-1-[[(1,1-Dimethylethoxy)Carbonyl]Amino]-2-Ethenyl-Cyclopropanecarboxylic Acid Methyl Ester;Cyclopropanecarboxylic acid,1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-,methyl ester,(1R,2S)-;SCHEMBL583727;DTXSID20439656;AMY38851;CS-B0405;(1R,2S)-Methyl1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate;AKOS016011333;N-Boc-(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester;methyl (1R,2S)-1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropane-1-carboxylate;CS-13008;A852729;N-Boc-(1 R,2 S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester;N-Boc-(1R, 2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester;N-Boc-(1R,2S)-amino-2-vinylcyclopropane Carboxylic Acid Methyl Ester;1-(tert-Butoxycarbonylamino)-2alpha-vinylcyclopropane-1alpha-carboxylic acid methyl ester;Methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-ethenylcyclopropane-1-carboxylate;cyclopropanecarboxylic acid,1-((1,1-dimethylethoxy)carbonylamino)-2-ethenyl-,methyl ester,(1r,2s)-;CYCLOPROPANECARBOXYLIC ACID,1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, METHYL ESTER, (1R,2S)-

Chemical Property of (1R,2S)-Methyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 312.253oC at 760 mmHg
• Flash Point: 142.646oC
• PSA: 68.12000
• Density: 1.101g/cm3
• LogP: 1.83320
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 241.13140809
• Heavy Atom Count: 17
• Complexity: 345

Purity/Quality:

97% ^*data from raw suppliers

(1R,2S)-Methyl1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1(CC1C=C)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@]1(C[C@H]1C=C)C(=O)OC

Technology Process of (1R,2S)-Methyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate

There total 23 articles about (1R,2S)-Methyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate 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: 92.0%

methanol (67-56-1) + (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid (159622-10-3,213316-50-8,259221-77-7) → (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester (159622-09-0,1201943-62-5,915317-20-3)

Guidance literature:

With diazomethyl-trimethyl-silane; In hexane; toluene; at 20 ℃; for 0.5h;

DOI:10.1007/s00726-015-2138-3

Reference yield: 84.0%

(1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid (159622-10-3,213316-50-8,259221-77-7) + diazomethyl-trimethyl-silane (18107-18-1) → (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester (159622-09-0,1201943-62-5,915317-20-3)

Guidance literature:

In methanol; diethyl ether; toluene; at 25 ℃; for 0.5h;

DOI:10.1039/c4ra12658k

Reference yield: 49.0%

1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester (1201943-62-5,915317-20-3) → (1S,2R)-1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid (259214-55-6,213316-50-8,259221-77-7) + (1S,2R)-1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester (1201943-62-5,915317-20-3) + (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid methyl ester (159622-09-0,1201943-62-5,915317-20-3)

Guidance literature:

With sodium hydroxide; alcalase 2.4L; potassium chloride; In water; acetone; at 35 - 38 ℃; for 139h; pH=8.1 - 8.3; Title compound not separated from byproducts;

DOI:10.1021/jo050468q

upstream raw materials:

(1S,2S)-1-Azidocarbonyl-2-vinyl-cyclopropanecarboxylic acid methyl ester

tert-butyl alcohol

1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid methyl ester

methanol

Downstream raw materials:

(1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid

(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt

(1R,2R)-methyl 1-t-butoxycarbonylamino-2-vinylcyclopropane carboxylate

(1R,2R)-methyl 1-amino-2-vinylcyclopropane carboxylate tosylate salt