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Hydrochloric Acid → (2-(N-(tert-Butyl)sulfamoyl)-5-propylphenyl)boronic acid

HRID 36266
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HRID 36266 반응식
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[B:23](OC(C)C)([O:28]C(C)C)[O:24]C(C)C.Cl>C1COCC1>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH3:17])=[CH:13][C:14]=1[B:23]([OH:28])[OH:24])(=[O:7])=[O:8])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 6470063N-tert-butyl-4-propylbenzenesulfonamideHCID 178418339Butyllithium

생성물 1

HCID 19939476(2-(N-(tert-Butyl)sulfamoyl)-5-propylphenyl)boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2.85 g (11.2 mmol) of N-t-butyl-4-n-propylbenzenesulfonamide (from Step A) in anhydrous THF (20 mL) cooled to -40° C. under N2 was added 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to room temperature and stirred for 2 hours. To the mixture, containing the bright red dianion at 0° C., was added triisopropyl borate (3.9 mL, 1.5 equiv). The next day, 2N HCl (3 mL) was added and the mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate. The organic solution was washed with 2N HCl, H2O and brine. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound; Rf =0.5 (1:1 EtOAc-hexane). The material was used in the next step without further purification.

후처리

  1. additionTo the mixture, containing the bright red dianion at 0° C.
  2. stirringthe mixture was stirred for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic solution was washed with 2N HCl, H2O and brine
  6. dry with materialThe organic phase was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f8b92982f24e4306880b1449ca19ff17
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05411980

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