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Sodium Hydroxide → HCID 86700881, Verbindung

HRID 881775
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 881775
[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[O:29][C:26]([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[O:29][C:26]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86700880HCID 86700880, Verbindung

Produkt 1

HCID 86700881HCID 86700881, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(4-(4′-((5-(tert-butyl)-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-7-oxabicyclo[2.2.1]heptan-1-yl)propanoate (100 mg, 0.21 mmol) in THF (3.4 mL) and methanol (0.85 mL) was added 1N NaOH solution (0.63 mL, 0.63 mmol) and the reaction was let stir at rt for 2 h. The resulting yellow reaction mixture was partially concentrated by rotary revaporation (rt water bath) to remove THF. The resulting yellow mixture was diluted with methanol, filtered and purified on preparative HPLC (10-50% acetonitrile:5 mM NH4OH) and lyophilized to afford 83 mg (86%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (s, 9H), 1.56-1.82 (m, 6H), 2.01-2.10 (m, 2H), 2.10-2.19 (m, 2H), 2.30-2.39 (m, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.60 (d, J=8.6 Hz, 2H), 7.62-7.67 (m, 4H) 10.51 (br. s., 1H). 13C NMR (100 MHz, DMSO-d6): δ ppm 174.5, 165.9, 159.5, 141.7, 138.3, 138.2, 133.1, 127.1, 125.8, 125.4, 117.1, 86.1, 85.5, 37.9, 34.9, 31.7, 30.2, 30.1, 27.8. ESI-MS m/z: 462.1 [M+H]+, retention time 1.13 min (condition E). HR/MS [M+H]+: found 462.2371. calc. 462.2393. RT: 1.96 (Condition L).

Aufarbeitung

  1. concentrationThe resulting yellow reaction mixture was partially concentrated by rotary revaporation (rt water bath)
  2. customto remove THF
  3. additionThe resulting yellow mixture was diluted with methanol
  4. filtrationfiltered
  5. custompurified on preparative HPLC (10-50% acetonitrile:5 mM NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-bf265115f7a1485b9b9a087f2e72a151
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993619B2

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