1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → HCID 22877900, Verbindung

HRID 1488858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488858
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.[N:54]1([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:61][CH2:60][CH2:59][C@H:55]1[C:56](O)=[O:57].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:62]([N:54]1[CH2:61][CH2:60][CH2:59][C@H:55]1[C:56]([NH2:28])=[O:57])([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63]

Komponenten

8

Edukt 4

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 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 22877900HCID 22877900, VerbindungAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride (998 mg, 2.65 mmols), 1,300 mg of a BOP reagent and 605 mg of Boc-L-Pro were dissolved in 50 ml of acetonitrile, and 0.8 ml of triethylamine were added thereto. The mixture was reacted at room temperature for 18 hours and at 50° C. for 20 hours. One-hundred milliliters of water and a small amount of sodium hydrogencarbonate were added thereto, and the resulting mixture was extracted with ethyl acetate. Subsequently, the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, dichloromethane), and then concentrated to produce 1,310 mg (2.44 mmols) of the final product in a yield of 92%.

Aufarbeitung

  1. customThe mixture was reacted at room temperature for 18 hours and at 50° C. for 20 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialSubsequently, the extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0e8b233837f34b73aa2d51c7e499b653
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674906

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