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

반응식

HRID 275422 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-57fd679929ab417a953abb3ddfc20d6a
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393771

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