Dimethylformamide → (S)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one

HRID 1992669Notes

Reaction equation

HRID 1992669 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:10][CH:9]=1.CN(C)C=O.[CH2:24]([C@H:31]1[CH2:35][O:34][C:33](=[O:36])[NH:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.[Cl-].[Li+]>ClCCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>[CH2:24]([C@H:31]1[CH2:35][O:34][C:33](=[O:36])[N:32]1[C:16](=[O:18])/[CH:15]=[CH:14]/[C:11]1[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

10

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 433294Lithium ChlorideHCID 6377974-Chlorocinnamic acidHCID 736225(S)-4-Benzyl-2-oxazolidinone

Product 1

HCID 10246725(S)-4-benzyl-3-[(2E)-3-(4-chlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

A solution of oxalyl chloride (10.82 mL, 124 mmol) in dichloromethane (50 mL) was added dropwise to a cooled solution of (2E)-3-(4-chlorophenyl)acrylic acid (11.33 g, 62.0 mmol) in dichloromethane (110 mL) and N,N-dimethylformamide (0.4 μL, 0.01 mmol). After stirring the reaction mixture for 24 hours, the solution was added dropwise to a cooled solution of (4S)-4-benzyl-1,3-oxazolidin-2-one (9.49 g, 53.6 mmol), triethylamine (39.2 mL, 282 mmol) and lithium chloride (11.95 g, 282 mmol) in dichloromethane (110 mL). The reaction mixture was slowly warmed to room temperature, stirred for 2 hours and then water (50 mL) was added. The mixture was diluted with dichloromethane (100 mL) and 5% citric acid solution (2×150 mL) was added. The phases were separated and the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by column chromatography on silica gel using dichloromethane as eluent afforded the desired product as a white solid, 14.6 g (74%).

Workup

  1. stirringstirred for 2 hours
  2. additionwas added
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-e178ede12b5e49c1bd5d34a9bd6d4ba9
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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