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Acetic Acid → HCID 68985012, Verbindung

HRID 1467895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1467895
[NH2:1][CH:2]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH:26]2[CH2:28][CH2:27]2)[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:37](C)=O.[Na+].CC(O)=O>CO.CCOC(C)=O>[CH:26]1([N:12]([CH:9]2[CH2:10][CH2:11][N:6]([C:4](=[O:5])[CH2:3][CH:2]([NH:1][CH3:37])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:7][CH2:8]2)[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:27][CH2:28]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68984655HCID 68984655, Verbindung

Produkt 1

HCID 68985012HCID 68985012, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of a compound 46 prepared in Example 30 (0.325 mmol, 150 mg) in methanol (5 mL) was added paraformaldehyde (0.813 mmol, 25 mg), Na(OAc)3BH and a catalytic amount of HOAc at room temperature. The resulting mixture was kept stirred at room temperature overnight. Then EtOAc (20 mL) was added to the mixture and the mixture was washed with saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 0% to 50% MeOH in DCM to afford the title compound 47. 1H NMR (CDCl3): δ 8.21 (d, J=8.1 Hz, 1H), 8.18 (br s, 1H), 8.04 (d, J=8.1 Hz, 1H), 7.87 (dd, J=7.84, 7.86 Hz, 1H), 4.63 (m, 1H), 4.15 (m, 1H), 3.95 (m, 1H), 3.52 (m, 1H), 3.23 (m, 1H), 2.90-2.55 (m, 3H), 2.70 (d, J=5.4 Hz, 3H), 2.07-1.54 (m, 8H), 1.00 (m, 6H), 0.92 (m, 2H), 0.80 (m, 2H). LC: 100%. MS: 490.2 (M+1).

Aufarbeitung

  1. customat room temperature
  2. washthe mixture was washed with saturated NaHCO3 and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified through a column of silica gel with a gradient of 0% to 50% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-3693db6d0eb34cf7a22cb2b3719fab7f
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000174B2

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