1,2-Dichloroethane → HCID 76674797, compound

HRID 407594Notes

Reaction equation

HRID 407594 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 dichloro-methane (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. LC-MS purity: >95%. (M+H)+ calcd: 885.4. found: 885.7.

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-b53e8ae1bda24b319b52d47f87ef7b70
Source dataset
uspto-grants-2014_06
Patent number
US08754106B2

Reaction notes

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