1,2-Dichloroethane → HCID 76674797、化合物

HRID 402198ノート

反応式

HRID 402198 の反応式
[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]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 739492-OxazolidinoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22149151CyclopropylmethanesulfonamideHCID 66870865HCID 66870865、化合物

生成物 1

HCID 76674797HCID 76674797、化合物収率 44.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a4ca04cfca334efc9a2c740c06a41039
出典データセット
uspto-grants-2014_06
特許番号
US08741926B2

反応ノート

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