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

HRID 83503Notes

Reaction equation

HRID 83503 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][CH:8]([C:12]([OH:14])=O)[CH2:7]1.[CH2:21]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[NH:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:21]([C@@H:28]1[CH2:32][O:31][C:30](=[O:33])[N:29]1[C:12]([CH:8]1[CH2:9][C:10](=[O:11])[N:6]([CH2:5][C:4]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:3]=2[O:2][CH3:1])[CH2:7]1)=[O:14])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 112544611-(2,4-Dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 71287868(R)-4-benzyl-3-[1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinoneYield 53.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (31.7 g) in chloroform (300 ml) were sequentially added (R)-4-benzyl-2-oxazolidinone (20.0 g), WSC.HCl (23.8 g) and 4-dimethylaminopyridine (6.90 g) under ice-cooling, the mixture was stirred for 15 minutes, warmed to room temperature and stirred for 18 hours. This reaction mixture was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/9) to give the titled compound (low-polarity component 26.4 g, high-polarity component 13.3 g).

Workup

  1. temperaturecooling
  2. stirringstirred for 18 hours
  3. customThis reaction mixture was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/9)

Sources & evidence

ORD record
ord-44cf240e5cb941fc87d690009273ac4d
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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