(4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one

Base Information

• Chemical Name: (4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one
• CAS No.: 1174715-53-7
• Molecular Formula: C₂₃H₂₁NO₃
• Molecular Weight: 359.425
• Mol file: 1174715-53-7.mol

Synonyms:(4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one

Chemical Property of (4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one

There total 1 articles about (4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-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: 61.0%

L-phenylalanine sodium salt (16480-57-2) + acetone (67-64-1) + naphthalene-1-carbonic acid chloride (879-18-5) → (4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one (1174715-53-7)

Guidance literature:

L-phenylalanine sodium salt; acetone; With trimethylaluminum; In toluene; at 0 - 20 ℃; for 15.08h; Molecular sieve; Inert atmosphere;

naphthalene-1-carbonic acid chloride; In toluene; for 2h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja9039604

Reference yield:

(4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one (1174715-53-7) + methyl trifluoromethanesulfonate (333-27-7) → (R)-4-benzyl-2,2-dimethyl-4-methyl-3-(1-naphthoyl)-oxazolidin-5-one (1174715-59-3) + (S)-4-benzyl-2,2-dimethyl-4-methyl-3-(1-naphthoyl)-oxazolidin-5-one (1174715-61-7)

Guidance literature:

(S)-4-benzyl-2,2-dimethyl-3-(1-naphthoyl)-oxazolidin-5-one; With potassium hexamethylsilazane; In tetrahydrofuran; 1,2-dimethoxyethane; at -78 ℃; for 0.05h; Inert atmosphere;

methyl trifluoromethanesulfonate; In tetrahydrofuran; 1,2-dimethoxyethane; at -78 ℃; for 0.166667h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja9039604

Reference yield:

(4S)-4-benzyl-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one (1174715-53-7) + 2-Fluorobenzaldehyde (446-52-6) → (4R)-4-benzyl-4-[(R)-(2-fluorophenyl)(hydroxy)methyl]-2,2-dimethyl-3-(naphthalene-1-carbonyl)-1,3-oxazolidin-5-one + C30H26FNO4

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.25h; Overall yield = 52 percent; Overall yield = 70 mg; stereoselective reaction; Inert atmosphere;

DOI:10.1002/hlca.202100127

upstream raw materials:

L-phenylalanine sodium salt

acetone

naphthalene-1-carbonic acid chloride

Downstream raw materials:

ethyle 2-((R)-2,2-dimethyl-4-(benzyl)-3-(1-naphthoyl)-5-oxooxazolidin-4-yl)-acetate

(R)-4-benzyl-2,2-dimethyl-4-methyl-3-(1-naphthoyl)-oxazolidin-5-one

(S)-4-benzyl-2,2-dimethyl-4-methyl-3-(1-naphthoyl)-oxazolidin-5-one