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Triacetoxyperiodinane → (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]amide

HRID 538649
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인쇄 미리보기

반응식

HRID 538649 반응식
[OH:1][CH2:2][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:13])[O:8][N:7]=1)([CH3:5])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:5][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[O:13])[O:8][N:7]=1)([CH3:4])[CH:2]=[O:1]
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참가 물질

5

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 67457548(S)-1-(tetrahydro-pyran-4-yl)pyrrolidine-2-carboxylic acid [3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]amide

생성물 1

HCID 117655527(S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]amide수율 52.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 516892
Sodium Bicarbonate
용매

실험 절차

To 180 mg (0.53 mmol) of (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-amide in DCM (1.74 mL) are added 317 mg (0.75 mmol) of (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin-periodinane). The reaction mixture is stirred at RT for 1 h, diluted with sat. aq. NaHCO3 solution and stirred for additonal 30 min. The layers are separated; the organic layer is washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure, the residue is purified by silica gel chromatographie (eluent: EE) to afford 93.0 mg of (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]amide. Yield: 52%; ESI-MS: 336 [M+H]+; HPLC (Rt): 1.12 min (method E)

후처리

  1. stirringstirred for additonal 30 min
  2. customThe layers are separated
  3. washthe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by silica gel chromatographie (eluent: EE)

출처 및 근거

ORD 기록
ord-231a0b4df2844ed28c62f0b7046b78f9
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865744B1

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