Sodium Hydroxide → HCID 10295657, Verbindung

HRID 1295128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295128
C([O:3][C:4](=[O:33])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C:20](=[O:32])[CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[CH2:28][CH2:27][CH2:26][NH:25][C:24]=4[N:23]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])C.[OH-].[Na+]>C1COCC1.O>[N:23]1[C:24]2[NH:25][CH2:26][CH2:27][CH2:28][C:29]=2[CH:30]=[CH:31][C:22]=1[CH2:21][C:20]([NH:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:33])=[O:3])[CH:11]=[CH:12]2)=[O:32]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67427797HCID 67427797, Verbindung

Produkt 1

HCID 10295657HCID 10295657, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-[5-(2-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl-acetylamino)-indol-1-yl]-hexanoic acid ethyl ester (50 mg, 0.12 mmol) in THF (1.0 mL) was added a solution of NaOH (18 mg, 0.45 mmol) in H2O (0.15 mL), and stirred at ambient temperature for 14 h. Solvents were evaporated. To the resulting residue was added 1N HCl until the solution reached a pH of 5. The mixture was extracted with EtOAc/DCM (9:1) several times until the aqueous layer was free from product by TLC. The extracts were combined, dried over Na2SO4, concentrated, and flash chromatographed on silica gel, eluting with MeOH/DCM (2.5, 5, and 7.5%) to afford the title compound (38 mg, 81% yield) as a pale brown solid. 1H NMR (CDCl3) δ 7.79 (d, 1H, J=1.9 Hz), 7.57 (d, 1H, J=7.3 Hz), 7.45 (d, 1H, J=8.9 Hz,), 7.34 (d, 1H, J=3.2 Hz), 7.23 (dd, 1H, J=2.0, 8.8 Hz), 6.69 (d, 1H, J=7.3 Hz), 6.46 (d, 1H, J=3.2 Hz), 3.83 (s, 0.9 H), 3.81 (s, 0.5H), 3.49 (t, 2H, J=5.6 Hz), 2.89 (d, 2H, J=7.2 Hz), 2.83 (t, 2H, J=6.1 Hz), 2.67–1.86 (m, 4H), 1.19–0.99 (m, 2H), 0.86 (t, 3H, J=7.3 Hz). Mass spectrum (LCMS, ESI) calculated for C24H29N4O3 421.2 (M+H); found 421.3.

Aufarbeitung

  1. customSolvents were evaporated
  2. additionTo the resulting residue was added 1N HCl until the solution
  3. extractionThe mixture was extracted with EtOAc/DCM (9:1) several times until the aqueous layer
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customflash chromatographed on silica gel
  7. washeluting with MeOH/DCM (2.5, 5, and 7.5%)

Quellen und Nachweise

ORD-Eintrag
ord-ca407e737a474dd0adb40245f3c68af4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241789B2

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