N-Phenylglycine ethyl ester → (4aR-cis)-1,2,3,4a,5,10b-Hexahydro-5,5-dimethyl-3-oxo-1-phenyl[1]benzopyrano[3,4-b][1,4]oxazine-9-carbonitrile

HRID 356676

反応式

HRID 356676 の反応式
C(OC(=O)CNC1C=CC=CC=1)C.C[Al](C)C.CC1(C)[C@@H]2O[C@@H]2C2C=C(C#N)C=CC=2O1.[C:33]([C:35]1[CH:36]=[CH:37][C:38]2[O:43][C:42]([CH3:45])([CH3:44])[C@H:41](O)[C@@H:40]([N:47]([CH2:54][C:55]([O:57]CC)=[O:56])[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:39]=2[CH:60]=1)#[N:34]>ClCCCl.C(OCC)(=O)C.C(Cl)(Cl)Cl.CO>[CH3:44][C:42]1([CH3:45])[C@@H:41]2[O:56][C:55](=[O:57])[CH2:54][N:47]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@@H:40]2[C:39]2[CH:60]=[C:35]([C:33]#[N:34])[CH:36]=[CH:37][C:38]=2[O:43]1

参加物

9

反応物 4

HCID 75190N-Phenylglycine ethyl esterHCID 10738551(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl esterHCID 10987295(1aR,7bR)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrileHCID 16682925Trimethylaluminum

生成物 1

HCID 67799274(4aR-cis)-1,2,3,4a,5,10b-Hexahydro-5,5-dimethyl-3-oxo-1-phenyl[1]benzopyrano[3,4-b][1,4]oxazine-9-carbonitrile

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane溶媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-phenylglycine ethyl ester (900 mg, 5.0 mmol) in 1,2-dichloroethane (10 mL) under argon at 20° C. was treated with trimethylaluminum (3.0 mL, 2.0M in toluene, 6.0 mmol) over 1-2 minutes. After 15 minutes, (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile (1.0 g, 5.0 mmol, title A compound of example 3) was added at once and stirring was continued for 1.5 hours. The mixture was diluted with ethyl acetate, quenched with a few drops of water and filtered through celite to remove gelatinous aluminum salts. The filtrate was washed with 5% sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate and concentrated. The residue was triturated with warm methanol to give warm methanol to give the title product (392 mg), mp 241°-243° C. [α]D =-129.1 ° (c=0.35 CHCl3). Analysis calculated for. C20H18N2O3 ·0.14 H2O: C,71.29; H,5.47; N, 8.31. Found: C, 71.05; H, 5.30; N, 8.55.

後処理

  1. waitwas continued for 1.5 hours
  2. customquenched with a few drops of water
  3. filtrationfiltered through celite
  4. customto remove gelatinous aluminum salts
  5. washThe filtrate was washed with 5% sodium bicarbonate, water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was triturated with warm methanol
  9. customto give

出典と根拠

ORDレコード
ord-a24d7fadbac848f990d1434e8d45cd9f
出典データセット
uspto-grants-1998_11
特許番号
US05837702

関連ノート

読み込み中…