Tert-butoxycarbonylalanine → HCID 22877896, Verbindung

HRID 1488860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488860
Cl.[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[N:28]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH:54]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C@H:55]([C:57](O)=[O:58])[CH3:56].C(=O)([O-])O.[Na+]>C(#N)C.O.C(N(CC)CC)C>[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:60]([NH:54][C@H:55]([C:57]([NH2:28])=[O:58])[CH3:56])([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61]

Komponenten

8

Edukt 4

HCID 85082Tert-butoxycarbonylalanineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 9976854(E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride

Produkt 1

HCID 22877896HCID 22877896, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride (1,053 mg, 2.65 mmols), 1,300 mg of a BOP reagent and 554 mg of Boc-L-Ala were dissolved in 50 ml of acetonitrile, and 0.8 ml of triethylamine were added thereto. The mixture was reacted at 60° C. for 17 hours. One-hundred milliliters of water and a small amount (about 10 g) of sodium hydrogencarbonate were added thereto, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, mixture of dichloromethane and ethyl acetate at a ratio of 20:1), and then concentrated to produce 1,085 mg (2.12 mmols) of the final product in a yield of 80%.

Aufarbeitung

  1. customThe mixture was reacted at 60° C. for 17 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified
  7. additioneluent, mixture of dichloromethane and ethyl acetate at a ratio of 20:1), and
  8. concentrationthen concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e0f0e0e4ace74e749050faf05b8838da
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674906

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