N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide

Base Information

• Chemical Name: N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide
• CAS No.: 129812-71-1
• Molecular Formula: C₂₂H₂₆ClN₅O₅
• Molecular Weight: 475.932

Synonyms:N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide

Chemical Property of N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide

Chemical Property:

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Technology Process of N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide

There total 6 articles about N^α-(tert-butoxycarbonyl)-N^β-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide 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: 81.0%

benzyl 6-chloro-2-formyl-5-methylpyrimidine-6-carboxylate (129812-70-0) + Boc-Dap(NH2)-CONH2 (75452-33-4) → Nα-(tert-butoxycarbonyl)-Nβ-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide (129812-71-1)

Guidance literature:

With 3 A molecular sieve; In acetonitrile; at 25 ℃; for 24h;

DOI:10.1021/jo00313a016

Reference yield:

(2S)-3-<(benzyloxy)amino>-2-<(tert-butoxycarbonyl)amino>propionamide (75624-25-8) → Nα-(tert-butoxycarbonyl)-Nβ-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide (129812-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / 10percent Pd/C / methanol / 4 h / 25 °C

2: 81 percent / 3-Angstroem molecular sieves / acetonitrile / 24 h / 25 °C

With 3 A molecular sieve; hydrogen; palladium on activated charcoal; In methanol; acetonitrile;

DOI:10.1021/jo00313a016

Reference yield:

(2S)-N-(benzyloxy)-2-azetidinone (71405-00-0) → Nα-(tert-butoxycarbonyl)-Nβ-<<(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)methylene>amino>-(S)-β-aminoalanineamide (129812-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NH₃ / methanol / 3 h / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / methanol / 4 h / 25 °C

3: 81 percent / 3-Angstroem molecular sieves / acetonitrile / 24 h / 25 °C

With 3 A molecular sieve; ammonia; hydrogen; palladium on activated charcoal; In methanol; acetonitrile;

DOI:10.1021/jo00313a016

upstream raw materials:

benzyl 6-chloro-2-formyl-5-methylpyrimidine-6-carboxylate

Boc-Dap(NH₂)-CONH₂

(E)-1-(6-carbethoxy-4-chloro-5-methylpyrimidin-2-yl)-2-phenylethylene

(2S)-3-<(benzyloxy)amino>-2-<(tert-butoxycarbonyl)amino>propionamide

Downstream raw materials:

N^α-(tert-butoxycarbonyl)-N^β-<1-ethoxy-3-(6-carbobenzoxy-4-chloro-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanineamide

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