N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^γ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid

Base Information

• Chemical Name: N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^γ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid
• CAS No.: 100430-92-0
• Molecular Formula: C₂₄H₃₁N₉O₅
• Molecular Weight: 525.567

Synonyms:N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^γ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid

Chemical Property of N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^γ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid

Chemical Property:

Purity/Quality:

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Technology Process of N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^γ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid

There total 8 articles about N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^γ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric 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: 93.0%

(S)-4-tert-Butoxycarbonylamino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyric acid ethyl ester (96846-13-8) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nγ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid (100430-92-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 - 25 ℃; for 4h;

DOI:10.1021/jm00146a008

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nγ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid (100430-92-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / NaOH / dioxane / 1 h / 50 - 55 °C

2: 1.) NH₃ (liq.), Na, 2.) (i-Pr)2NEt / 1.) -60 deg C, 10 min, 2.) H₂O, dioxane, RT, overnight

3: 83 percent / (i-Pr)2NEt / dimethylformamide / 120 h / 20 - 25 °C

4: 97 percent / H₂ / 5percent Pd/C / ethanol / 760 Torr / Ambient temperature

5: 79 percent / N,N-dimethyl-acetamide / 144 h

6: 93 percent / NaOH / ethanol / 4 h / 20 - 25 °C

With sodium hydroxide; ammonia; hydrogen; sodium; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jm00146a008

Reference yield:

N2-<(1,1-dimethylethoxy)carbonyl>-N4-<(4-methylphenyl)sulfonyl>-2,3-diaminobutanoic acid (13558-07-1) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nγ-(tert-butyloxycarbonyl)-L-2,4-diaminobutyric acid (100430-92-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NH₃ (liq.), Na, 2.) (i-Pr)2NEt / 1.) -60 deg C, 10 min, 2.) H₂O, dioxane, RT, overnight

2: 83 percent / (i-Pr)2NEt / dimethylformamide / 120 h / 20 - 25 °C

3: 97 percent / H₂ / 5percent Pd/C / ethanol / 760 Torr / Ambient temperature

4: 79 percent / N,N-dimethyl-acetamide / 144 h

5: 93 percent / NaOH / ethanol / 4 h / 20 - 25 °C

With sodium hydroxide; ammonia; hydrogen; sodium; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jm00146a008

upstream raw materials:

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid

4--L-2,4-diaminobutyric acid

(S)-4-tert-Butoxycarbonylamino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyric acid ethyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-2,4-diaminobutyric acid

(S)-4-Amino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyric acid; compound with trifluoro-acetic acid

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