N^δ-(tert-butyloxycarbonyl)-N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine

Base Information

• Chemical Name: N^δ-(tert-butyloxycarbonyl)-N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine
• CAS No.: 143745-29-3
• Molecular Formula: C₂₇H₃₂FN₅O₆
• Molecular Weight: 541.579

Synonyms:N^δ-(tert-butyloxycarbonyl)-N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine

Chemical Property of N^δ-(tert-butyloxycarbonyl)-N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N^δ-(tert-butyloxycarbonyl)-N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine

There total 9 articles about N^δ-(tert-butyloxycarbonyl)-N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine 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:

4-amino-5-fluoro-2-methylquinazoline (137553-47-0) → Nδ-(tert-butyloxycarbonyl)-Nα-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine (143745-29-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / 37percent aq. HCl / 2-methoxy-ethanol / 15 h / 100 °C

2: 1.) 90percent HNO₃, 95percent H₂SO₄, 2.) H₂ / 2.) Raney Ni / 1.) from 0 deg C to RT, 13 h, 2.) 2-methoxyethanol

3: 30 percent / 70percent aq. AcOH / Raney Ni

4: 93 percent / aq. HCl / 31 h / 75 - 80 °C

5: 29 h / Ambient temperature

6: Et₃N / dimethylformamide / 0.33 h / 0 °C

7: Et₃N / dimethylformamide / 22 h / 0 - 20 °C

8: 10percent aq. NH₄OH / 6 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; sulfuric acid; hydrogen; nitric acid; acetic acid; triethylamine; nickel; In 2-methoxy-ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00100a013

Reference yield:

3,4-dihydro-5-fluoro-2-methyl-4-oxoquinazoline (143745-24-8) → Nδ-(tert-butyloxycarbonyl)-Nα-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine (143745-29-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 90percent HNO₃, 95percent H₂SO₄, 2.) H₂ / 2.) Raney Ni / 1.) from 0 deg C to RT, 13 h, 2.) 2-methoxyethanol

2: 30 percent / 70percent aq. AcOH / Raney Ni

3: 93 percent / aq. HCl / 31 h / 75 - 80 °C

4: 29 h / Ambient temperature

5: Et₃N / dimethylformamide / 0.33 h / 0 °C

6: Et₃N / dimethylformamide / 22 h / 0 - 20 °C

7: 10percent aq. NH₄OH / 6 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; sulfuric acid; hydrogen; nitric acid; acetic acid; triethylamine; nickel; In N,N-dimethyl-formamide;

DOI:10.1021/jm00100a013

Reference yield:

6-amino-3,4-dihydro-5-fluoro-2-methyl-4-oxoquinazoline (143745-26-0) → Nδ-(tert-butyloxycarbonyl)-Nα-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine (143745-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 30 percent / 70percent aq. AcOH / Raney Ni

2: 93 percent / aq. HCl / 31 h / 75 - 80 °C

3: 29 h / Ambient temperature

4: Et₃N / dimethylformamide / 0.33 h / 0 °C

5: Et₃N / dimethylformamide / 22 h / 0 - 20 °C

6: 10percent aq. NH₄OH / 6 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; acetic acid; triethylamine; nickel; In N,N-dimethyl-formamide;

DOI:10.1021/jm00100a013

upstream raw materials:

N^δ-(tert-butoxycarbonyl)-L-ornithine

4-amino-5-fluoro-2-methylquinazoline

3,4-dihydro-5-fluoro-2-methyl-4-oxoquinazoline

6-amino-3,4-dihydro-5-fluoro-2-methyl-4-oxoquinazoline

Downstream raw materials:

N^α-(2-desamino-2-methyl-5-fluoro-5,8-dideazaisopterroyl)-L-ornithine

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