(3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid

Base Information

• Chemical Name: (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid
• CAS No.: 865704-59-2
• Molecular Formula: C₂₃H₂₄N₂O₇
• Molecular Weight: 440.453
• Mol file: 865704-59-2.mol

Synonyms:(3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid

Chemical Property of (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid

There total 8 articles about (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic 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:

4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid (865704-45-6) → (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid (865704-59-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 50 percent / P₂O₅ / CHCl₃ / 60 h / 20 °C

2.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

4.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

5.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

6.1: toluene / Heating

7.1: 0.82 g / toluene / Heating

8.1: 96 percent / TFA / CH₂Cl₂ / 20 °C

With sodium azide; hydrogen; sodium hexamethyldisilazane; phosphorus pentoxide; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; toluene; 6.1: Curtius rearrangement;

DOI:10.1055/s-2005-865362

Reference yield:

tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate (865704-46-7) → (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid (865704-59-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaI; NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 60 percent / tetrahydrofuran / 4 h / -95 - -75 °C

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

3.1: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

4.1: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

5.1: toluene / Heating

6.1: 0.82 g / toluene / Heating

7.1: 96 percent / TFA / CH₂Cl₂ / 20 °C

With sodium azide; hydrogen; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 5.1: Curtius rearrangement;

DOI:10.1055/s-2005-865362

Reference yield:

1-benzyl 5-tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}pentanedioate (865704-48-9) → (3S)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-({[(benzyloxy)carbonyl]amino}methyl)-4-oxobutanoic acid (865704-59-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C / 760 Torr

2: Et₃N / tetrahydrofuran / 0.5 h / -15 - 20 °C

3: aq. NaN₃ / tetrahydrofuran / 1 h / 0 °C

4: toluene / Heating

5: 0.82 g / toluene / Heating

6: 96 percent / TFA / CH₂Cl₂ / 20 °C

With sodium azide; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 4: Curtius rearrangement;

DOI:10.1055/s-2005-865362

upstream raw materials:

4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoic acid

tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate

(3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-tert-butoxy-5-oxopentanoic acid

1-benzyl 5-tert-butyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}pentanedioate

Downstream raw materials:

(S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid

benzyl (3S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1-pyrrolidinecarboxylate

Refernces