Sodium Thiosulfate → (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate

HRID 1907269노트

반응식

HRID 1907269 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][CH:21]([OH:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59190371tert-butyl (S)-1-(4-bromophenyl)ethyl(4-hydroxy-4-phenylbutyl)carbamate

생성물 1

HCID 59190380(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate수율 73.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of tert-butyl (S)-1-(4-bromophenyl)ethyl(4-hydroxy-4-phenylbutyl)carbamate (3.24 g, 7.1 mmol) in CH2Cl2 (20 mL) at rt was added 15% Dess-Martin periodinane solution in CH2Cl2 (23 mL, 10.8 mmol). The mixture was stirred overnight at rt. Satd aq NaHCO3 (50 mL) was added and the mixture was stirred for 10 min. Solid Na2S2O3 (5 g) was added and stirring was continued for 1 h. The mixture was extracted with CH2Cl2 (2×100 mL) and the combined organic layer was washed with brine (35 mL) and dried over Na2SO4. Removal of the solvent left an amber oil (3.19 g) which was purified by chromatography on a 40-g silica cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (2.32 g, 72%) as a yellow oil. LC-MS Method 1 tR=2.40 min, m/z=470, 468, 348, 346.

후처리

  1. stirringthe mixture was stirred for 10 min
  2. stirringstirring
  3. waitwas continued for 1 h
  4. extractionThe mixture was extracted with CH2Cl2 (2×100 mL)
  5. washthe combined organic layer was washed with brine (35 mL)
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent
  8. waitleft an amber oil (3.19 g) which
  9. customwas purified by chromatography on a 40-g silica cartridge
  10. washeluted with a 0-100% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-ce2d91b46f8d4f808d5ced612efb76d4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598160B2

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