N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester

Base Information

• Chemical Name: N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester
• CAS No.: 459871-10-4
• Molecular Formula: C₃₄H₄₈N₆O₉S
• Molecular Weight: 716.856

Synonyms:N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester

Chemical Property of N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester

Chemical Property:

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Technology Process of N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester

There total 10 articles about N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester 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: 45.0%

(4S,5R)-3-((methylthio)acetyl)-4-methyl-5-phenyl-2-oxazolidinone + Nα-(tert-butoxycarbonyl)-Nβ-[[(4-amino-6-(carboethoxy)-5-methylpyrimidin-2-yl)methylene]amino]-(S)-β-aminoalanine tert-butyl ester → Nα-(tert-butoxycarbonyl)-Nβ-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester (459871-10-4)

Guidance literature:

(4S,5R)-3-((methylthio)acetyl)-4-methyl-5-phenyl-2-oxazolidinone; With tin(II) trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78 - -20 ℃;

N^α-(tert-butoxycarbonyl)-N^β-[[(4-amino-6-(carboethoxy)-5-methylpyrimidin-2-yl)methylene]amino]-(S)-β-aminoalanine tert-butyl ester; In tetrahydrofuran; at -5 ℃; for 2h; Further stages.;

DOI:10.1021/ja012741l

Reference yield:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) → Nα-(tert-butoxycarbonyl)-Nβ-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester (459871-10-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / pyridine / 0.08 h / 25 °C

2.1: 70 percent / NaN₃; tetrabutylammonium bromide / dimethylformamide / 0.17 h / 70 °C

3.1: 95 percent / H₂ / Pd/C / ethanol / 15 h / 25 °C

4.1: 97 percent / 3 A molecular sieves / acetonitrile / 24 h

5.1: Sn(OTf)2; diisopropylethylamine / tetrahydrofuran / -78 - -20 °C

5.2: 45 percent / tetrahydrofuran / 2 h / -5 °C

With tin(II) trifluoromethanesulfonate; sodium azide; 3 A molecular sieve; tetrabutylammomium bromide; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja012741l

Reference yield:

ethyl 6-chloro-2-formyl-5-methylpyrimidine-4-carboxylate (74536-28-0) → Nα-(tert-butoxycarbonyl)-Nβ-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]-2-methylthiopropion-3-yl]-(S)-β-aminoalanine tert-butyl ester (459871-10-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 70 percent / NaBH₄ / ethanol / 0.5 h / 0 - 5 °C

2.1: 86 percent / NaN₃ / dimethylformamide / 6 h / 0 - 5 °C

3.1: 95 percent / H₂ / 10percent Pd/C / ethanol / 2 h / 25 °C / 760.05 Torr

4.1: 40 percent / MnO₂ / acetonitrile / 2 h / 75 °C

5.1: 97 percent / 3 A molecular sieves / acetonitrile / 24 h

6.1: Sn(OTf)2; diisopropylethylamine / tetrahydrofuran / -78 - -20 °C

6.2: 45 percent / tetrahydrofuran / 2 h / -5 °C

With manganese(IV) oxide; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; sodium azide; 3 A molecular sieve; hydrogen; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja012741l

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

ethyl 6-chloro-2-formyl-5-methylpyrimidine-4-carboxylate

tert-butyl 2-<(tert-butoxycarbonyl)amino>-3-aminopropanoate

ethyl 4-amino-2-(hydroxymethyl)-5-methylpyrimidine-6-carboxylate

Downstream raw materials:

N^α-(tert-butoxycarbonyl)-N^β-[3(S)-(4-amino-6-carboethoxy-5-methylpyrimidin-2-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl]propion-3-yl]-(S)-β-aminoalanine tert-butyl ester

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