2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

Base Information

• Chemical Name: 2-((tert-Butoxycarbonyl)amino)but-3-enoic acid
• CAS No.: 171077-04-6
• Molecular Formula: C9H15NO4
• Molecular Weight: 201.22
• European Community (EC) Number: 868-766-6
• Mol file: 171077-04-6.mol

Synonyms:171077-04-6;2-((tert-Butoxycarbonyl)amino)but-3-enoic acid;2-[(tert-butoxycarbonyl)amino]-3-butenoic acid;2-[(2-methylpropan-2-yl)oxycarbonylamino]but-3-enoic Acid;MFCD02682487;Boc-D-Vinylglycine;N-Boc-L-alpha-vinylglycine;SCHEMBL6291036;BYHZVVBUNVWRGH-UHFFFAOYSA-N;CGA46891;MFCD02682489;AKOS022646700;AT29164;n-(tert-butoxycarbonyl)-2-vinylglycine;SY253189;2-((tert-Butoxycarbonyl)amino)but-3-enoicacid;EN300-314154;2-{[(tert-butoxy)carbonyl]amino}but-3-enoic acid

Chemical Property of 2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

Chemical Property:

• PSA: 79.12000
• LogP: 1.35470
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 201.10010796
• Heavy Atom Count: 14
• Complexity: 242

Purity/Quality:

99%min ^*data from raw suppliers

2-[(tert-butoxycarbonyl)amino]-3-butenoicacid 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(C=C)C(=O)O

Technology Process of 2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

There total 6 articles about 2-((tert-Butoxycarbonyl)amino)but-3-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: 82.0%

N-tert-butoxycarbonyl-N-(1-hydroxymethyl-2-propenyl)amine (169324-82-7) → (+/-)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-butenoic acid (171077-04-6)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone;

DOI:10.1002/1521-3773(20020503)41:9<1614::AID-ANIE1614>3.0.CO;2-5

Reference yield:

3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one (115148-32-8) → (+/-)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-butenoic acid (171077-04-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / ceric ammonium nitrate / acetonitrile; H₂O

2: 88 percent / triethylamine / CH₂Cl₂

3: 88 percent / Cs₂CO₃ / methanol

4: 82 percent / CrO₃; H₂SO₄ / H₂O; acetone

With chromium(VI) oxide; ammonium cerium(IV) nitrate; sulfuric acid; caesium carbonate; triethylamine; In methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1002/1521-3773(20020503)41:9<1614::AID-ANIE1614>3.0.CO;2-5

Reference yield:

4-vinyloxazolidin-2-one (144634-45-7) → (+/-)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-butenoic acid (171077-04-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / triethylamine / CH₂Cl₂

2: 88 percent / Cs₂CO₃ / methanol

3: 82 percent / CrO₃; H₂SO₄ / H₂O; acetone

With chromium(VI) oxide; sulfuric acid; caesium carbonate; triethylamine; In methanol; dichloromethane; water; acetone;

DOI:10.1002/1521-3773(20020503)41:9<1614::AID-ANIE1614>3.0.CO;2-5

upstream raw materials:

di-tert-butyl dicarbonate

2-amino-3-butenoic acid

N-tert-butoxycarbonyl-N-(1-hydroxymethyl-2-propenyl)amine

3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one

Downstream raw materials:

vinylglycine trifluoroacetate

Refernces

• 1、 Hallinan, Keith O.,Crout, David H. G.,Errington, William. "Simple Synthesis of L- and D-Vinylglycine (2-Aminobut-3-enoic Acid) and Related Amino Acid". . p. 3537 - 3544. Retrieved 2007/10/02.