1,2-Dichloroethane → HCID 49853916, compound

HRID 1400039Notes

Reaction equation

HRID 1400039 reaction equation
[C:1]12([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:9][CH:8]=3)[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.[O:24]=[C:25]([C:29]1[O:30][CH:31]=[CH:32][CH:33]=1)[C:26](O)=[O:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[O:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:25](=[O:24])[C:26]([N:3]1[CH2:4][CH:5]2[C:1]([C:7]3[CH:8]=[CH:9][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:11][CH:12]=3)([CH2:6]2)[CH2:2]1)=[O:27]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 738462-Furylglyoxylic acidHCID 757711-HydroxybenzotriazoleHCID 67515007HCID 67515007, compound2×

Product 1

HCID 49853916HCID 49853916, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (163 mg, 0.46 mmol), in DMF (20 mL), were added α-oxo-2-furanacetic acid (65 mg, 0.46 mmol), EDC (97 mg, 0.51 mmol), HOBt (69 mg, 0.51 mmol) and NMM (0.11 mL, 1.02 mmol) at 0° C. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, DMF was evaporated in vacuo and residue was dissolved in chloroform (50 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.4:9.6 MeOH:CHCl3) to provide the title compound (140 mg, 69%) as white solid.

Workup

  1. customOn completion, DMF was evaporated in vacuo and residue
  2. dissolutionwas dissolved in chloroform (50 mL)
  3. washThe organic layer was washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, 0.4:9.6 MeOH:CHCl3)

Sources & evidence

ORD record
ord-464ef2908c5d4e37868b47d06c669103
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

Loading…