(1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid

Base Information

• Chemical Name: (1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid
• CAS No.: 259214-55-6
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• European Community (EC) Number: 889-559-7
• DSSTox Substance ID: DTXSID00463398
• Wikidata: Q82288267
• Mol file: 259214-55-6.mol

Synonyms:259214-55-6;(1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-, (1S,2R)-;(1S,2R)-2-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylic Acid;Cyclopropanecarboxylic acid,1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-,(1S,2R)-;SCHEMBL2617514;DTXSID00463398;AMY40325;CS-B0184;MFCD06795884;(1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylicacid;1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-,(1S,2R)-;AKOS016843104;(1S,2R)-1-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-ethenyl-cyclopropanecarboxylic acid;(1S,2R)-1-((t-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid;(1S,2R)-1-(Tert-Butoxycarbonylamino)-2-Vinylcyclopropanecarboxylic Acid;(1S, 2R)-2-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylic acid;(1S,2R)-1-(tert-Butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid, AldrichCPR;(1S,2R)-1-[(tert-Butoxycarbonyl)amino]-2-ethenylcyclopropane-1-carboxylic acid;cyclopropanecarboxylic acid,1-((1,1-dimethylethoxy)carbonylamino)-2-ethenyl-,(1s,2r)-

Chemical Property of (1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 3.43E-06mmHg at 25°C
• Melting Point: 99-100.5 °C
• Boiling Point: 361°C at 760 mmHg
• PKA: 4.95±0.50(Predicted)
• Flash Point: 172.1°C
• PSA: 79.12000
• Density: 1.17g/cm³
• LogP: 1.74480
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 331

Purity/Quality:

98.0%Min ^*data from raw suppliers

(1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylicacid 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)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@]1(C[C@@H]1C=C)C(=O)O

Technology Process of (1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid

There total 19 articles about (1S,2R)-1-((tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid 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: 98.0%

→ (1S,2R)-1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid (259214-55-6,213316-50-8,259221-77-7)

Guidance literature:

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

Reference yield:

(1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate (213316-49-5) → (1S,2R)-1-tert-butoxycarbonylamino-2-vinylcyclopropanecarboxylic acid (259214-55-6,213316-50-8,259221-77-7) + N-Boc-(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester (259217-95-3,213316-49-5)

Guidance literature:

(1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate; With sodium hydroxide; disodium hydrogenphosphate; phosphoric acid; acalase 2.4L; In water; dimethyl sulfoxide; at 26 - 40 ℃; for 41.1667h; pH=8 - 8.5;

With sulfuric acid; In water; pH=2; Conversion of starting material;

upstream raw materials:

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

(1RS,2SR)-ethyl 2-vinyl-1-(tert-butoxycarbonylamino)cyclopropanecarboxylate

(1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

C₁₃H₁₂ClN₃O*C₇H₈O₃S

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

Refernces

• 1、 -. "MACROCYCLIC SERINE PROTEASE INHIBITORS". . . Retrieved 2010/11/03.
• 2、 -. "Inhibitors of Hepatitis C Virus". Page/Page column 20-21. . Retrieved 2008/12/04.