2-Furancarboxylic acid, 5-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-phenylethyl]-

Base Information

• Chemical Name: 2-Furancarboxylic acid, 5-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-phenylethyl]-
• CAS No.: 828259-70-7
• Molecular Formula: C18H21NO5
• Molecular Weight: 331.368
• Mol file: 828259-70-7.mol

Synonyms:

Chemical Property of 2-Furancarboxylic acid, 5-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-phenylethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Furancarboxylic acid, 5-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-phenylethyl]-

There total 5 articles about 2-Furancarboxylic acid, 5-[(1S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-phenylethyl]- 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%

[1-(5-formyl-furan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (866045-97-8) → 5-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-furan-2-carboxylic acid (828259-70-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In water; acetonitrile; at 0 ℃; for 4h;

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → 5-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-furan-2-carboxylic acid (828259-70-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran

1.2: tetrahydrofuran

2.1: H₂; NaBH₄; (CH₂NH₂)2 / Ni(OAc)2*4H₂O / ethanol

3.1: CSA / methanol

4.1: pyridine

5.1: pyridinium chlorochromate / CH₂Cl₂

6.1: K₂CO₃ / methanol

7.1: SO₃-pyridine; Et₃N; DMSO / CH₂Cl₂

8.1: NaClO₂; NaH₂PO₄; H₂O₂ / acetonitrile

With pyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; potassium carbonate; dimethyl sulfoxide; ethylenediamine; triethylamine; pyridinium chlorochromate; nickel diacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1055/s-2004-834807

Reference yield:

[(S)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-but-3-ynyl]-carbamic acid tert-butyl ester (828259-55-8) → 5-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-furan-2-carboxylic acid (828259-70-7)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂; NaBH₄; (CH₂NH₂)2 / Ni(OAc)2*4H₂O / ethanol

2: CSA / methanol

3: pyridine

4: pyridinium chlorochromate / CH₂Cl₂

5: K₂CO₃ / methanol

6: SO₃-pyridine; Et₃N; DMSO / CH₂Cl₂

7: NaClO₂; NaH₂PO₄; H₂O₂ / acetonitrile

With pyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; potassium carbonate; dimethyl sulfoxide; ethylenediamine; triethylamine; pyridinium chlorochromate; nickel diacetate; In methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1055/s-2004-834807

upstream raw materials:

[1-(5-formyl-furan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Boc-L-phenylalaninal

[(S)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-but-3-ynyl]-carbamic acid tert-butyl ester