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Sodium hydride → tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate

HRID 525106
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HRID 525106 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:20]1[N:21]=[CH:22][N:23]=[C:24]2[C:31]=1[C:30]1[CH2:29][CH2:28][CH2:27][C:26]=1[S:25]2>C1COCC1>[CH3:16][N:8]([CH:5]1[CH2:6][CH2:7][CH:2]([O:1][C:20]2[N:21]=[CH:22][N:23]=[C:24]3[C:31]=2[C:30]2[CH2:29][CH2:28][CH2:27][C:26]=2[S:25]3)[CH2:3][CH2:4]1)[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 78981712-Chloro-7-thia-9,11-diazatricyclo(6.4.0.0,2,6)dodeca-1(12),2(6),8,10-tetraeneHCID 219251474-(N-Boc-N-methylamino)cyclohexanol

생성물 1

HCID 68110120tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate수율 74.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl N-(4-hydroxycyclohexyl)-N-methylcarbamate (447 mg, 1.95 mmol, 1.30 equiv) in anhydrous THF (30 mL), then sodium hydride (300 mg, 7.50 mmol, 5.00 equiv, 60% dispersion in mineral oil) was added and stirring for 20 min at room temperature under nitrogen. Then 12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraene (316 mg, 1.50 mmol, 1.00 equiv) was added and stirred for 6 h at ambient temperature. The reaction mixture was quenched with NH4Cl (sat.) at 0° C., diluted with brine, extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by a silica gel column with EA/PE (1:10-1:4) to provide tert-butyl N-methyl-N-(4-[7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yloxy]cyclohexyl)carbamate (450 mg, 74%) as a white solid. MS: (ES, m/z): 404 [M+H]+.

후처리

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringstirred for 6 h at ambient temperature
  4. customThe reaction mixture was quenched with NH4Cl (sat.) at 0° C.
  5. additiondiluted with brine
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration and concentration
  10. customthe residue was purified by a silica gel column with EA/PE (1:10-1:4)

출처 및 근거

ORD 기록
ord-0210bef3cc0344a8871b125f04cf92b2
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340554B2

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