(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-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-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone
CAS No.:133645-51-9
Molecular Formula:C₂₃H₃₂N₂O₆
Molecular Weight:432.517
Hs Code.:

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

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

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

There total 13 articles about (4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-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: 70.0%

: 69610-41-9,117625-90-8
Boc-L-Pro-H

: 3-(2-bromopropionyl)-4R-methyl-5S-phenyloxazolidin-2-one

: 133645-51-9
(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: With tristriphenylphosphine cobalt chloride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo010530t

Reference yield: 67.0%

: 69610-41-9,117625-90-8
Boc-L-Pro-H

: 133645-51-9
(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.75h;

Boc-L-Pro-H; With phosphate buffer; In dichloromethane; at -78 - 0 ℃; pH=7;

With water; dihydrogen peroxide; more than 3 stages;

Reference yield:

: 37577-28-9,58550-13-3,757124-50-8
(1S,2R)-(+)-norphedrine

: 133645-51-9
(4R,5S,2'R,3'R,2S)-3-[3'-(N-tert-butoxycarbonyl-2-pyrrolidinyl)-3-hydroxy-2'-methylpropanoyl]-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 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

With n-butyllithium; phosphate buffer; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium methylate; triethylamine;
DOI:10.1055/s-1996-4296