benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate

Base Information

• Chemical Name: benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate
• CAS No.: 756531-84-7
• Molecular Formula: C₂₁H₂₄N₂O₅
• Molecular Weight: 384.432
• Mol file: 756531-84-7.mol

Synonyms:benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate

Chemical Property of benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate

There total 9 articles about benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate 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:

glutaric anhydride, (108-55-4) → benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate (756531-84-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 24 percent / NEt₃; DMAP; N-hydroxysuccinimide / toluene / 24 h / Heating

2.1: tBuCOCl; NEt₃ / tetrahydrofuran / 2 h / -30 °C

2.2: 90 percent / LiCl / tetrahydrofuran / -30 - 20 °C

3.1: LHDMS / tetrahydrofuran / 1 h / -78 °C

3.2: 55 percent / tetrahydrofuran / 20 h / -50 °C

4.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h

5.1: Et₃N; DPPA / toluene

5.2: 75 percent / toluene / 16 h / Heating

6.1: 93 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

7.1: 93 percent / NaHCO₃; Bu₄NI / dimethylformamide / 20 h / 20 °C

8.1: TFA; TES / CH₂Cl₂ / 2 h / 20 °C

9.1: CDI / tetrahydrofuran / 5 h

9.2: 2.63 g / NH₃ / tetrahydrofuran

With dmap; lithium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; diphenyl-phosphinic acid; hydrogen; dihydrogen peroxide; pivaloyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; triethylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/hlca.200490142

Reference yield:

5-(tert-butoxy)-5-oxopentanoic acid (63128-51-8) → benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate (756531-84-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tBuCOCl; NEt₃ / tetrahydrofuran / 2 h / -30 °C

1.2: 90 percent / LiCl / tetrahydrofuran / -30 - 20 °C

2.1: LHDMS / tetrahydrofuran / 1 h / -78 °C

2.2: 55 percent / tetrahydrofuran / 20 h / -50 °C

3.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h

4.1: Et₃N; DPPA / toluene

4.2: 75 percent / toluene / 16 h / Heating

5.1: 93 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

6.1: 93 percent / NaHCO₃; Bu₄NI / dimethylformamide / 20 h / 20 °C

7.1: TFA; TES / CH₂Cl₂ / 2 h / 20 °C

8.1: CDI / tetrahydrofuran / 5 h

8.2: 2.63 g / NH₃ / tetrahydrofuran

With lithium hydroxide; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; diphenyl-phosphinic acid; hydrogen; dihydrogen peroxide; pivaloyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; triethylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/hlca.200490142

Reference yield:

(R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-4-[(tert-butoxy)carbonyl]-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-13-4) → benzyl (S)-4-(aminocarbonyl)-2-({[(benzyloxy)carbonyl]amino}methyl)butanoate (756531-84-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / H₂ / Pd/C / tetrahydrofuran / 1.5 h

2.1: Et₃N; DPPA / toluene

2.2: 75 percent / toluene / 16 h / Heating

3.1: 93 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

4.1: 93 percent / NaHCO₃; Bu₄NI / dimethylformamide / 20 h / 20 °C

5.1: TFA; TES / CH₂Cl₂ / 2 h / 20 °C

6.1: CDI / tetrahydrofuran / 5 h

6.2: 2.63 g / NH₃ / tetrahydrofuran

With lithium hydroxide; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; diphenyl-phosphinic acid; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; triethylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/hlca.200490142

upstream raw materials:

glutaric anhydride,

5-(tert-butoxy)-5-oxopentanoic acid

(R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-4-[(tert-butoxy)carbonyl]-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-[(tert-butoxy)carbonyl]butanoic acid

Downstream raw materials:

benzyl (S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-{[(triphenylmethyl)amino]carbonyl}butanoate