Trifluoroacetic acid → 4-[9-(Benzoylamino)-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamido]-5-oxopentanoic acid

HRID 2230455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230455
[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:22]([NH:24][CH:25]([CH:35]=[O:36])[CH2:26][CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:37])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:22]([NH:24][CH:25]([CH:35]=[O:36])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:37])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 54215480t-Butyl 4-[9-(benzoylamino)-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino-[1,2-a][1,2]diazepine-1-carboxamido]-5-oxopentanoate

Produkt 1

HCID 543661774-[9-(Benzoylamino)-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamido]-5-oxopentanoic acidAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of t-butyl ester 234e (179 mg, 0.35 mmol) in dry CH2Cl2 (3 ml) was cooled to 0° C. and treated with trifluoroacetic acid (2 ml). The resultng solution was stirred at 0° C. for 30 min and then at room temperature for 2 h. The solution was concentrated, the residue taken up in dry CH2Cl2 (5 ml) and the mixture again concentrated. This process was repeated once again with more CH2Cl2 (5 ml). The residue obtained was crystallized in diethyl ether. The precipitate was collected and purified on silica gel column (5% methanol in CH2Cl2) which afforded compound 235e as a white solid (111 mg, 70%): mp 142° C. (dec); [α]D20 −85.5 (c 0.062, MeOH); IR (KBr) 3409, 3075, 2952, 1651, 1541, 1424, 1280, 1198, 1136, 717; 1H NMR (D6-DMSO) δ9.40 (1H, s), 8.62 (2H, m), 7.96-7.38 (5H, m), 5.19-5.02 (1H, m), 4.98-4.79 (1H, m), 4.48-4.19 (1H, m), 3.51-3.11 (2H, m), 3.04-2.90 (2H, m), 2.38-1.46 (10H, m).

Aufarbeitung

  1. waitat room temperature for 2 h
  2. concentrationThe solution was concentrated
  3. concentrationthe mixture again concentrated
  4. customThe residue obtained
  5. customwas crystallized in diethyl ether
  6. customThe precipitate was collected
  7. custompurified on silica gel column (5% methanol in CH2Cl2) which

Quellen und Nachweise

ORD-Eintrag
ord-def3bf2e199949dbb7c9c33d4271c610
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423840B1

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