1,2-Dichloroethane → HCID 67980747, compound

HRID 1400037Notes

Reaction equation

HRID 1400037 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]1[C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=[N:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[O:24]1[C:28]([C:29]([N:3]2[CH2:4][CH:5]3[C:1]([C:7]4[CH:8]=[CH:9][C:10]([N:13]5[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]5=[O:23])=[CH:11][CH:12]=4)([CH2:6]3)[CH2:2]2)=[O:30])=[CH:27][CH:26]=[N:25]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 20605991,2-Oxazole-5-carboxylic acidHCID 67515007HCID 67515007, compound2×

Product 1

HCID 67980747HCID 67980747, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 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) (200 mg, 0.57 mmol), in DMF (10 mL), were added isoxazole-5-carboxylic acid (71 mg, 0.63 mmol), EDC (130 mg, 0.68 mmol), HOBt (89 mg, 0.68 mmol) and NMM (0.19 mL, 1.71 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 (156 mg, 67%) 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-64c7a978e52b48cd9c946d58a73e19fb
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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