(S)-4-Benzyl-2-oxazolidinone → (S)-4-Benzyl-3-[(S)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone

HRID 83527

Reaction equation

HRID 83527 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]([C@H: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 736225(S)-4-Benzyl-2-oxazolidinoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112544611-(2,4-Dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 86680364(S)-4-Benzyl-3-[(S)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinoneYield 54.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (20 g) prepared according to the same procedures as Preparation 5 in chloroform (200 ml) were sequentially added (S)-4-benzyl-2-oxazolidinone (15.2 g) and WSC.HCl (16.4 g), 4-(dimethylamino)pyridine (4.4 g) at room temperature, and the mixture was stirred for 3 hours. This reaction solution was washed with a 5 wt % aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/3), subjected to azeotropic drying with toluene, and dried under reduced pressure to give the titled compound (17.2 g).

Workup

  1. customat room temperature
  2. washThis reaction solution was washed with a 5 wt % aqueous solution of sodium hydrogen carbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/3)
  6. dry with materialto azeotropic drying with toluene
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-fe9aac0101e04f9ea94e4a4d82e87b01
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

Loading…