1,2-Dichloroethane → HCID 76674797, compound

HRID 531381Notes

Reaction equation

HRID 531381 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19][CH:20]3[CH2:38][CH:37]4[N:22]([C:23](=[O:52])[N:24]([CH2:43][C:44]5[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=5)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([OH:42])=O)([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:21]3)[C:16]3[C:11](=[C:12]([CH3:55])[C:13]([O:53][CH3:54])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].C(Cl)CCl.O1CCNC1=O.C1(C[S:70]([NH2:73])(=[O:72])=[O:71])CC1.[CH2:74]1[CH2:84][CH2:83]N2C(=NCCC2)C[CH2:75]1>ClCCl>[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19][CH:20]3[CH2:38][CH:37]4[N:22]([C:23](=[O:52])[N:24]([CH2:43][C:44]5[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=5)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:73][S:70]([C:74]6([CH3:75])[CH2:83][CH2:84]6)(=[O:72])=[O:71])=[O:42])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:21]3)[C:16]3[C:11](=[C:12]([CH3:55])[C:13]([O:53][CH3:54])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 739492-OxazolidinoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 221491511-CyclopropylmethanesulfonamideHCID 66870865HCID 66870865, compound

Product 1

HCID 76674797HCID 76674797, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To acid 138 (212 mg, 0.276 mmol) dissolved in dichloromethane (7 mL) was added EDC (69 mg, 0.359 mmol) and the reaction mixture was stirred at room temperature. After 7 hours TLC and LC-MS indicated complete conversion of the starting material into the corresponding oxazolidinone. The reaction mixture was diluted with dichloromethane (20 mL) and the organic phase was washed twice with water after which the organic phase was dried, filtered, and concentrated. The residue was dissolved in dichloromethane (5 mL) and cyclopropylmethyl sulfonamide (53 mg, 0.394 mmol) and DBU (78 μL, 0.525 mmol) were added and the reaction mixture was stirred at room temperature for 20 hours. The mixture was diluted with dichloromethane (30 mL) and the organic phase was washed twice with 10% citric acid and once with brine. The organic phase was dried, filtered and concentrated and the crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1, 1:2, ethyl acetate, ethyl acetate/methanol 9:1) to give the title compound (108 mg, 44%) as a colorless solid.

Workup

  1. washthe organic phase was washed twice with water after which the organic phase
  2. customwas dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  6. stirringthe reaction mixture was stirred at room temperature for 20 hours
  7. washthe organic phase was washed twice with 10% citric acid and once with brine
  8. customThe organic phase was dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customthe crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1, 1:2, ethyl acetate, ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-11ca258f7b5842039395705035f5270e
Source dataset
uspto-grants-2016_05
Patent number
US09353103B2

Reaction notes

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