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

Base Information

• Chemical Name: (R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one
• CAS No.: 637337-54-3
• Molecular Formula: C₂₇H₃₃NO₅
• Molecular Weight: 451.563
• Mol file: 637337-54-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 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: 90.0%

5-(tert-butoxy)-5-oxopentanoic acid (63128-51-8) + (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one (191090-32-1) → (R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-54-3)

Guidance literature:

5-(tert-butoxy)-5-oxopentanoic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -30 ℃; for 2h;

(R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one; With lithium chloride; In tetrahydrofuran; at -30 - 20 ℃;

DOI:10.1002/hlca.200490142

Reference yield:

glutaric anhydride, (108-55-4) → (R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-54-3)

Guidance literature:

Multi-step reaction with 2 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

With dmap; 1-hydroxy-pyrrolidine-2,5-dione; pivaloyl chloride; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1002/hlca.200490142

Reference yield: 55.0%

benzyl iodoacetate (81867-37-0) + (R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-54-3) → (R)-3-((R)-2-{[(benzyloxy)carbonyl]methyl}-4-[(tert-butoxy)carbonyl]-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-13-4)

Guidance literature:

(R)-3-{4-[(tert-butoxy)carbonyl]-1-oxobutyl}-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

benzyl iodoacetate; In tetrahydrofuran; at -50 ℃; for 20h;

DOI:10.1002/hlca.200490142

upstream raw materials:

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

(R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one

glutaric anhydride,

Downstream raw materials:

(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

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

1-benzyl 5-(tert-butyl) (S)-2-({[(benzyloxy)carbonyl]amino}methyl)pentanedioate