Acetonitrile → (3S-trans)-[2-[(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-pyran-4yl)amino]phenyl]carbamic acid, ethyl ester

HRID 275422

反応式

HRID 275422 の反応式
[CH3:1][C:2]1([CH3:15])[C@H:7]2[O:8][C@H:6]2[C:5]2C=C(C#N)C=[CH:12][C:4]=2[O:3]1.[CH2:16]([O:18][C:19]([NH:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24])=[O:20])[CH3:17].Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.C(#[N:42])C>C(OCC)(=O)C>[C:12]([C:4]1[O:3][C:2]([CH3:1])([CH3:15])[C@@H:7]([OH:8])[C@H:6]([NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[NH:21][C:19](=[O:20])[O:18][CH2:16][CH3:17])[CH:5]=1)#[N:42]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 24840Magnesium perchlorateHCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrileHCID 122150062-[(Ethoxycarbonyl)amino]aniline

生成物 1

HCID 67845190(3S-trans)-[2-[(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-pyran-4yl)amino]phenyl]carbamic acid, ethyl ester収率 92.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

The reaction mixture containing (1aS-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile, from example 2, part A (1.0 g, 5.0 mmol), 2-[(ethoxycarbonyl)amino]aniline, compound of example 1, part B (900 mg, 5.0 mmol) and magnesium perchlorate (1.12 g, 5.0 mmol) in acetonitrile (5.0 mL) was stirred under argon at room temperature for 48 hours. The reaction mixture was diluted with ethyl acetate and washed with water, saturated sodium bicarbonate solution and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated to give a colorless foam which was purified by flash chromatography (25% ethyl acetate in hexanes) to yield the title product as an amorphous solid (1.76 g, 92.8%) (shrinks at 84° C.). [a]D =+21° (c=1.1%, MeOH). Microanalysis calculated for C21H23N3O4 : C,66.13; H, 6.08; N,11.02. Found: C, 66.11 ; H, 6.15; N, 10.78.

後処理

  1. washwashed with water, saturated sodium bicarbonate solution and brine
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customto give a colorless foam which
  5. customwas purified by flash chromatography (25% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-57fd679929ab417a953abb3ddfc20d6a
出典データセット
uspto-grants-1995_02
特許番号
US05393771

関連ノート

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