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Sodium hydride → 2-[2-(5-Bromo-2-fluoro-phenyl)-3,3-difluoro-2-(2-nitro-benzenesulfonylamino)-propoxy]-2-methyl-propionic acid tert-butyl ester

HRID 81584
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HRID 81584 반응식
[OH:1][C:2]([CH3:11])([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([F:39])=[C:19]([C:21]2([CH:36]([F:38])[F:37])[CH2:23][N:22]2[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])[CH:20]=1>CN(C=O)C.C1COCC1>[C:6]([O:5][C:3](=[O:4])[C:2]([O:1][CH2:23][C:21]([C:19]1[CH:20]=[C:15]([Br:14])[CH:16]=[CH:17][C:18]=1[F:39])([NH:22][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])[CH:36]([F:38])[F:37])([CH3:11])[CH3:10])([CH3:9])([CH3:8])[CH3:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 118940tert-Butyl 2-hydroxyisobutyrateHCID 866502672-(5-Bromo-2-fluorophenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine

생성물 1

HCID 666658022-[2-(5-Bromo-2-fluoro-phenyl)-3,3-difluoro-2-(2-nitro-benzenesulfonylamino)-propoxy]-2-methyl-propionic acid tert-butyl ester수율 81%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl α-hydroxyisobutyrate (533 mg, 3.32 mmol) in 4.5 mL DMF and 0.75 mL THF was added portion wise (133 mg, 3.32 mmol) sodium hydride at room temperature. After the reaction mixture had been stirring for 15 minutes, a solution of 2-(5-bromo-2-fluoro-phenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine (1 g, 2.22 mmol) was added. The reaction mixture was stirred at rt for 150 minutes and quenched with aqueous NH4Cl solution. TBME was added, the layers were separated, washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/EtOAc 6/1->5/1 to give 1.10 g of the title compound as a pale yellow resin.

후처리

  1. stirringThe reaction mixture was stirred at rt for 150 minutes
  2. customquenched with aqueous NH4Cl solution
  3. additionTBME was added
  4. customthe layers were separated
  5. washwashed with brine and TBME
  6. dry with materialThe combined organic layers were dried over MgSO4.H2O
  7. customevaporated
  8. customThe crude product was purified on a silica gel column
  9. washby eluting with hexane/EtOAc 6/

출처 및 근거

ORD 기록
ord-62670c4f90854884b0ac3e4eb52e055d
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846658B2

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