tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 145902-56-3
• Molecular Formula: C₂₈H₄₄N₂O₆
• Molecular Weight: 504.667
• Mol file: 145902-56-3.mol

Synonyms:tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Chemical Property of tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

There total 14 articles about tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 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: 79.0%

L-leucine tert-butyl ester hydrochloride (2748-02-9,13081-32-8) + (4R,5S)-4-benzyl-3-[(tert-butoxy)carbonyl]-2,2-dimethyl-1,3-oxazolidine-5-carboxylic acid (139397-07-2) → tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (145902-56-3)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃;

DOI:10.1021/jm00054a004

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (145902-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 10N NaOH, Na₂CO₃ / H₂O; tetrahydrofuran / Ambient temperature

2: KHCO₃ / dimethylformamide / 12 h

3: TsOH / 36 h / Ambient temperature

4: aq. LiOH / methanol; tetrahydrofuran

5: 79 percent / HOBt, N-methylmorpholine, DCC / dimethylformamide / 25 °C

With 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; sodium carbonate; benzotriazol-1-ol; potassium hydrogencarbonate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a004

Reference yield:

D-phenylalanine methyl ester hydrochloride (13033-84-6) → tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (145902-56-3)

Guidance literature:

Multi-step reaction with 9 steps

1: NaHCO₃ / H₂O; tetrahydrofuran / Ambient temperature

2: diisobutylaluminium hydride / toluene; hexane / -77 °C

3: sodium metabisulfite / H₂O / 5 h / Ambient temperature

4: 25percent aq. HCl / 12 h / 80 °C

5: 10N NaOH, Na₂CO₃ / H₂O; tetrahydrofuran / Ambient temperature

6: KHCO₃ / dimethylformamide / 12 h

7: TsOH / 36 h / Ambient temperature

8: aq. LiOH / methanol; tetrahydrofuran

9: 79 percent / HOBt, N-methylmorpholine, DCC / dimethylformamide / 25 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; sodium hydroxide; sodium disulfite; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; potassium hydrogencarbonate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00054a004

upstream raw materials:

L-leucine tert-butyl ester hydrochloride

(4R,5S)-4-benzyl-3-[(tert-butoxy)carbonyl]-2,2-dimethyl-1,3-oxazolidine-5-carboxylic acid

di-tert-butyl dicarbonate

D-phenylalanine methyl ester hydrochloride

Downstream raw materials:

(2(S)-hydroxy-3(R)-amino-4-phenylthiobutanoyl)-L-leucine trifluoroacetate

Bestatin hydrochloride

bestatin trifluroacetate salt