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

HRID 1519719ノート

反応式

HRID 1519719 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-2e38d95c0119441aac9bc1ea3d2b3f8b
出典データセット
uspto-grants-2015_07
特許番号
US09073821B2

反応ノート

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