(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

Base Information

• Chemical Name: (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate
• CAS No.: 71460-02-1
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID10473564
• Nikkaji Number: J1.008.044D
• Wikidata: Q72470059
• Mol file: 71460-02-1.mol

Synonyms:71460-02-1;(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate;MFCD07368399;Methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate;methyl (S)-2-((tert-butoxycarbonyl)amino)pent-4-ynoate;methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-ynoate;Methyl (S)-2-(Boc-amino)-4-pentynoate;(S)-2-(Boc-amino)-4-pentynoic acid methyl ester;SCHEMBL879326;(S)-Methyl2-((tert-butoxycarbonyl)amino)pent-4-ynoate;DTXSID10473564;QPMUXIIQQHTMKO-QMMMGPOBSA-N;WCA46002;AC9020;(2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester;AKOS016014579;(S)-methyl 2-(BOC-amino)pent-4-ynoate;BS-17502;CS-0137050;(S)-2-(Boc-amino)-4-pentynoic acid methyl ester ee;methyl (S)-2-[[(1,1-dimethylethoxy)-carbonyl]amino]pent-4-ynoate;methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pent-4-ynoate;methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate;Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-pentynoate, AldrichCPR

Chemical Property of (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

Chemical Property:

• PSA: 64.63000
• LogP: 1.46690
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 308

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-Methyl2-((tert-butoxycarbonyl)amino)pent-4-ynoate 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)NC(CC#C)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC#C)C(=O)OC

Technology Process of (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

There total 27 articles about (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate 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%

methanol (67-56-1) + di-tert-butyl dicarbonate (24424-99-5) + (2S)-2-amino-4-pentynoic acid (23235-01-0) → methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate (71460-02-1,173306-82-6)

Guidance literature:

methanol; (2S)-2-amino-4-pentynoic acid; With thionyl chloride; at 0 - 20 ℃;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; Saturated solution;

Reference yield: 97.0%

propargyl bromide (106-96-7) + acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester (173306-81-5) → methyl 2-[((1,1-dimethylethoxy)carbonyl)amino]-4-pentynoate (71460-02-1,173306-82-6)

Guidance literature:

With zinc; In N,N-dimethyl-formamide; at 20 - 25 ℃;

DOI:10.1016/S0040-4039(00)73067-X

Reference yield: 96.0%

(S)-methyl 2-((tert-butoxycarbonyl)amino)-5-(triisopropylsilyl)pent-4-ynoate → methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate (71460-02-1,173306-82-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1002/anie.201610426

upstream raw materials:

propargyl bromide

acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

di-tert-butyl dicarbonate

propargyclycine methyl ester hydrochloride

Downstream raw materials:

2-tert-Butoxycarbonylamino-5-(2,4-difluoro-phenyl)-pent-4-ynoic acid methyl ester

(+/-)-methyl 2-(tert-butoxycarbonylamino)-5-phenylpent-4-ynoate

methyl 5-(2-aminophenyl)-2-[(tert-butoxycarbonyl)amino]-4-pentynoate

Methyl 2-N-boc-amino-5-(4-morpholinophenyl)-pent-4-ynoate