4-((tert-Butoxycarbonyl)amino)but-2-enoic acid

Base Information

• Chemical Name: 4-((tert-Butoxycarbonyl)amino)but-2-enoic acid
• CAS No.: 180913-22-8
• Molecular Formula: C9H15 N O4
• Molecular Weight: 201.222
• European Community (EC) Number: 833-977-4
• Nikkaji Number: J1.511.317K
• Mol file: 180913-22-8.mol

Synonyms:180913-22-8;4-((tert-Butoxycarbonyl)amino)but-2-enoic acid;89711-09-1;(E)-4-[(2-methylpropan-2-yl)oxycarbonylamino]but-2-enoic acid;(E)-4-((tert-Butoxycarbonyl)amino)but-2-enoic acid;(2E)-4-([(tert-Butoxy)carbonyl]amino)but-2-enoic acid;trans 4-{[(tert-butoxy)carbonyl]amino}but-2-enoic acid;2-Butenoicacid,4-[[(1,1-dimethylethoxy)carbonyl]amino]-,(2E)-(9CI);(2E)-4-{[(tert-butoxy)carbonyl]amino}but-2-enoic acid;2-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2E)-;4-{[(tert-butoxy)carbonyl]amino}but-2-enoic acid;SCHEMBL10323475;SCHEMBL10323476;MUQOCUSTNGBFJL-SNAWJCMRSA-N;AKOS027321570;AT11494;EN300-209610;(E)-4-(tertbutoxycarbonylamino)but-2-enoic acid;EN300-1590649;(e)-4-((t-butoxycarbonyl)amino)but-2-enoic acid;(E)-4-(tert-butoxycarbonylamino)but-2-enoic acid;A1-03161;N-tert-butyloxycarbonyl-(E)-4-amino-2-butenoic acid;F9994-0692

Chemical Property of 4-((tert-Butoxycarbonyl)amino)but-2-enoic acid

Chemical Property:

• Boiling Point: 373.4±35.0 °C(Predicted)
• PKA: 4.49±0.10(Predicted)
• PSA: 75.63000
• Density: 1.132±0.06 g/cm3(Predicted)
• LogP: 1.54280
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 201.10010796
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

99%min ^*data from raw suppliers

trans 4-{[(tert-Butoxy)carbonyl]amino}but-2-enoic acid 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)NCC=CC(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)NC/C=C/C(=O)O

Technology Process of 4-((tert-Butoxycarbonyl)amino)but-2-enoic acid

There total 1 articles about 4-((tert-Butoxycarbonyl)amino)but-2-enoic 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:

tert-butyl N-(2,3-dihydroxypropyl)carbamate (137618-48-5) → (trans)-4-[(t-butoxycarbonyl)amino]-2-butenoic acid (180913-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium periodate / water / 1 h / 20 °C / Darkness

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.33 h / 0 °C

2.2: 1 h / 20 °C

3.1: lithium hydroxide / water; tetrahydrofuran / 20 °C

With sodium periodate; sodium hydride; lithium hydroxide; In tetrahydrofuran; water; mineral oil;

DOI:10.1002/anie.202109769

Reference yield: 90.0%

benzylamine (100-46-9) + (trans)-4-[(t-butoxycarbonyl)amino]-2-butenoic acid (180913-22-8) → tert-butyl (E)-(4-(benzylamino)-4-oxobut-2-en-1-yl)carbamate

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/acs.joc.9b01936

Reference yield: 82.0%

(R)-5-(2-methyl-4-phenoxyphenyl)-4-oxo-N-(piperidin-3-yl)-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamide + (trans)-4-[(t-butoxycarbonyl)amino]-2-butenoic acid (180913-22-8) → (R,E)-tert-butyl (4-(3-(5-(2-methyl-4-phenoxyphenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamido)piperidin-1-yl)-4-oxobut-2-en-1-yl)carbamate

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

upstream raw materials:

tert-butyl N-(2,3-dihydroxypropyl)carbamate

Refernces