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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
ノート
印刷プレビュー

反応式

HRID 538649 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 516892
Sodium Bicarbonate
溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-231a0b4df2844ed28c62f0b7046b78f9
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08865744B1

反応ノート

読み込み中…

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