4-Nitrobenzenesulfonyl chloride → tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylate

HRID 1669393ノート

反応式

HRID 1669393 の反応式
[Si]([O:8][CH2:9][C@H:10]1[CH2:12][N:11]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.CCN(CC)CC.[N+:50]([C:53]1[CH:58]=[CH:57][C:56]([S:59](Cl)(=[O:61])=[O:60])=[CH:55][CH:54]=1)([O-:52])=[O:51]>C1COCC1.CCOCC.CN(C1C=CN=CC=1)C.C(Cl)Cl>[N+:50]([C:53]1[CH:54]=[CH:55][C:56]([S:59]([O:8][CH2:9][C@H:10]2[CH2:12][N:11]2[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])(=[O:61])=[O:60])=[CH:57][CH:58]=1)([O-:52])=[O:51]

参加物

9

反応物 5

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 11033505tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)aziridine-1-carboxylate

生成物 1

HCID 53381222tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylate収率 57%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 21868444Ether tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)aziridine-1-carboxylate (prepared following literature procedures: Travins, J. M.; Etzkorn, F. A. Tetrahedron Lett. 1998, 39, 9389-9392) in THF/Et2O (1/1) (0.17 M) was cooled in an ice bath and treated dropwise over 20 min with 1 M TBAF in THF (1.05 eq). The resulting solution was stirred in the ice bath for 30 min, before being quenched by the addition of sat. aq. NaHCO3 and extracted into Et2O/PE (4/1). The organic layers were collected, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was taken up in dry DCM (0.17 M) and Et3N (1.3 eq) introduced prior to cooling to 0° C. DMAP (0.1 eq) and 4-nitrobenzenesulfonyl chloride (1.1 eq) were added and the resulting mixture left to stir at RT overnight. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3, water and brine before drying over Na2SO4, filtering and concentrating in vacuo. The crude was purified by FC (PE/EtOAc 8:2) to afford the title compound as an off-white solid (57%). (ES+) m/z 359 (M+H)+.

後処理

  1. custombefore being quenched by the addition of sat. aq. NaHCO3
  2. extractionextracted into Et2O/PE (4/1)
  3. customThe organic layers were collected
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. waitthe resulting mixture left
  9. washwashed with sat. aq. NaHCO3, water and brine
  10. dry with materialbefore drying over Na2SO4
  11. filtrationfiltering
  12. concentrationconcentrating in vacuo
  13. customThe crude was purified by FC (PE/EtOAc 8:2)

出典と根拠

ORDレコード
ord-776a2d5e362246ccaafdd35e6a5be3d6
出典データセット
uspto-grants-2011_08
特許番号
US07989438B2

反応ノート

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