Sulfuric Acid → (2S)-N-hydroxy-2-{[(4-{[5-(methoxymethyl)furan-3-yl]ethynyl}phenyl)carbonyl](methyl)amino}-N',2-dimethylpropanediamide

HRID 1519719노트

반응식

HRID 1519719 반응식
S(=O)(=O)(O)O.[CH3:6][O:7][CH2:8][C:9]1[O:13][CH:12]=[C:11]([C:14]#[C:15][C:16]2[CH:41]=[CH:40][C:19]([C:20]([N:22]([CH3:39])[C@:23]([CH3:38])([C:28]([NH:30][O:31]C3CCCCO3)=[O:29])[C:24]([NH:26][CH3:27])=[O:25])=[O:21])=[CH:18][CH:17]=2)[CH:10]=1.C(=O)([O-])O.[Na+].[Cl-].[Na+]>O.C(OCC)(=O)C.O1CCOCC1>[OH:31][NH:30][C:28](=[O:29])[C@:23]([N:22]([C:20]([C:19]1[CH:40]=[CH:41][C:16]([C:15]#[C:14][C:11]2[CH:10]=[C:9]([CH2:8][O:7][CH3:6])[O:13][CH:12]=2)=[CH:17][CH:18]=1)=[O:21])[CH3:39])([CH3:38])[C:24]([NH:26][CH3:27])=[O:25]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 86679283(2S)-2-[(4-{[5-(methoxymethyl)furan-3-yl]ethynyl}benzoyl)(methyl)amino]-N,2-dimethyl-N'-(tetrahydro-2H-pyran-2-yloxy)propanediamide

생성물 1

HCID 86679284(2S)-N-hydroxy-2-{[(4-{[5-(methoxymethyl)furan-3-yl]ethynyl}phenyl)carbonyl](methyl)amino}-N',2-dimethylpropanediamide수율 70%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

A 1 mol/L sulfuric acid aqueous solution (2.6 mL) was added dropwise, under water cooling, to a 1,4-dioxane (4.0 mL) solution of (2S)-2-[(4-{[5-(methoxymethyl)furan-3-yl]ethynyl}benzoyl)(methyl)amino]-N,2-dimethyl-N′-(tetrahydro-2H-pyran-2-yloxy)propanediamide (0.43 g) as obtained in Example 18-(4), and the mixture was stirred for 3 hours and 45 minutes at room temperature. Ethyl acetate and water were added, and the mixture was adjusted to pH 6 with a saturated aqueous solution of sodium hydrogen carbonate. Then, sodium chloride was added, and the organic layer was isolated. The extract was washed with brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=100/0→80/20) to obtain (2S)-N-hydroxy-2-{[(4-{[5-(methoxymethyl)furan-3-yl]ethynyl}phenyl)carbonyl](methyl)amino}-N′,2-dimethylpropanediamide (Compound 550, white solid) (0.25 g, 68%).

후처리

  1. customthe organic layer was isolated
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThen, the desiccant was filtered out
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=100/0→80/20)

출처 및 근거

ORD 기록
ord-2e38d95c0119441aac9bc1ea3d2b3f8b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073821B2

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