1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (R)-4-benzyl-3-[(trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone

HRID 83484Notes

Reaction equation

HRID 83484 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[C@@H:9]([CH3:12])[C@H:8]([C:13]([OH:15])=O)[CH2:7]1.[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[NH:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[N:30]1[C:13]([C@H:8]1[C@H:9]([CH3:12])[C:10](=[O:11])[N:6]([CH2:5][C:4]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:3]=2[O:2][CH3:1])[CH2:7]1)=[O:15])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 86680344HCID 86680344, compound

Product 1

HCID 86680347(R)-4-benzyl-3-[(trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinoneYield 54.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of the crude product of (trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carboxylic acid (14.0 g) in chloroform (60 ml) were sequentially added (R)-4-benzyl-2-oxazolidinone (8.15 g), WSC.HCl (9.70 g), 4-dimethylaminopyridine (2.81 g), and the mixture was stirred overnight at room temperature. This reaction solution was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 1/3) to give the titled compound (low-polarity component 11.4 g, high-polarity component 10.1 g).

Workup

  1. customThis reaction solution was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 1/3)

Sources & evidence

ORD record
ord-e98c16645566452c92bdcbab1fcb12bb
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

Loading…