(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone
• CAS No.: 180715-99-5
• Molecular Formula: C₂₄H₃₄N₂O₆
• Molecular Weight: 446.544
• Mol file: 180715-99-5.mol

Synonyms:(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property of (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

There total 10 articles about (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone 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: 97.0%

trimethoxonium tetrafluoroborate (420-37-1) + (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone (133645-51-9) → (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone (180715-99-5)

Guidance literature:

trimethoxonium tetrafluoroborate; (4R,5S,2'R,3'R,2"S)-3-[3'-(N-tert-butoxycarbonyl-2"-pyrrolidinyl)-3"-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone; With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at 20 ℃; for 24h;

With water; at 0 ℃;

Reference yield: 35.0%

N,N,N',N'-tetramethyl-1,8-diaminonaphthalene (20734-58-1) + (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone (133645-51-9) → (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone (180715-99-5)

Guidance literature:

With trimethoxonium tetrafluoroborate; In dichloromethane; at 0 - 20 ℃; for 50h; Inert atmosphere; Molecular sieve;

Reference yield:

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) → (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3'-methoxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone (180715-99-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) MeONa / 1.) toluene, reflux, 2.) toluene, reflux, 3 h

2: 1.) BuLi / 1.) THF, hexane, from -75 to -70 deg C, 2.) THF, hexane, from -80 to -55 deg C, 2.5 h

3: 1.) Et₃N, (Bu)2BOTf, 2.) phosphate buffer, 30percent aq. H₂O₂

4: 83 percent / molecular sieves 4A, proton sponge / CH₂Cl₂ / 48 h / 0 - 20 °C

With n-butyllithium; phosphate buffer; Proton Sponge; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium methylate; triethylamine; In dichloromethane;

DOI:10.1055/s-1996-4296

upstream raw materials:

trimethoxonium tetrafluoroborate

(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Boc-L-Pro-H

4-methyl-5-phenyloxazolidin-2-one

Downstream raw materials:

N-Boc-(2R,3R,4S)-dolaproine

tert-butyl (S)-2-((1R,2R)-1-methoxy-3-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate