Triethylamine → HCID 67274143, Verbindung

HRID 599767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599767
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:36](O)=[O:37])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:22]([CH3:35])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[N:72]1([CH:78]2[CH2:83][CH2:82][N:81]([CH2:84][C:85]([O:87][CH2:88][CH3:89])=[O:86])[CH2:80][CH2:79]2)[CH2:77][CH2:76][NH:75][CH2:74][CH2:73]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:21]=[C:22]([CH3:35])[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:24]([CH3:26])[CH:25]=3)[C:36]([N:75]3[CH2:76][CH2:77][N:72]([CH:78]4[CH2:83][CH2:82][N:81]([CH2:84][C:85]([O:87][CH2:88][CH3:89])=[O:86])[CH2:80][CH2:79]4)[CH2:73][CH2:74]3)=[O:37])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 25208036(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylateHCID 54188692HCID 54188692, Verbindung

Produkt 1

HCID 67274143HCID 67274143, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2.80 g (4.90 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1g), 1.80 g (5.61 mmol) TBTU and 3.10 mL (22.08 mmol) triethylamine in 30 mL DMF was stirred for 1 h at RT. Then 2.00 g (5.48 mmol) ethyl (4-piperazin-1-yl-piperidin-1-yl)-acetate were added. The reaction mixture was stirred for 1 h at RT, poured onto 150 mL 15% K2CO3 solution and extracted with 200 mL EtOAc. The organic phase was extracted with 150 mL of 10% citric acid solution, the aqueous phase was made alkaline with 15% K2CO3 solution and extracted with 200 mL EtOAc. The organic phase was concentrated by evaporation i.vac. and the residue was purified by chromatography (silica gel, EtOH).

Aufarbeitung

  1. extractionextracted with 200 mL EtOAc
  2. extractionThe organic phase was extracted with 150 mL of 10% citric acid solution
  3. extractionextracted with 200 mL EtOAc
  4. concentrationThe organic phase was concentrated by evaporation i.vac
  5. customand the residue was purified by chromatography (silica gel, EtOH)

Quellen und Nachweise

ORD-Eintrag
ord-8fe1cc7a4a404a8eb5babb22b37465e8
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897603B2

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