StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 356676
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a24d7fadbac848f990d1434e8d45cd9f
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05837702

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion