HCID 52933910, Verbindung → HCID 52934135, Verbindung

HRID 1024477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024477
[C:1]([C:3]([C:6]1[CH:36]=[CH:35][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:23][C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30]C)=[O:29])=[O:25])=[N:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2]>C1COCC1.CO.O.[OH-].[Li+]>[C:1]([C:3]([C:6]1[CH:36]=[CH:35][C:9]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[S:23][C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:33])[CH3:34])[C:28]([OH:30])=[O:29])=[O:25])=[N:21][CH:20]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:8][CH:7]=1)([CH3:4])[CH3:5])#[N:2]

Komponenten

5

Edukt 1

HCID 52933910HCID 52933910, Verbindung

Produkt 1

HCID 52934135HCID 52934135, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 168937Lithium hydroxide, monohydrateLösungsmittel

Versuchsvorschrift

To methyl 2-(5-(4-(4-(2-cyanopropan-2-yl)benzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (Example 85, 65 mg) in THF (1 ml), methanol (1 ml) and 1M lithium hydroxide monohydrate (0.51 ml) was added and reaction mixture was stirred overnight at RT. Organic solvent was concentrated and added water, dilute HCl was added under stirring to pH acidic. The reaction mixture was filtered, to obtain the title compound. Yield: 22 mg (35%). 1HNMR (DMSO-d6, 300 MHz): δ 13.0 (bs, 1H), 10.49 (s, 1H), 8.4 (s, 1H), 8.37 (d, 1H), 8.04 (d, 2H), 7.93 (d, 2H), 7.81 (d, 2H), 7.71 (d, 2H), 4.31 (m, 1H), 2.25 (m, 1H), 1.74 (s, 6H), 0.97 (m, 6H); MS (ES+) m/z 491.2 (M+1).

Aufarbeitung

  1. customreaction mixture
  2. concentrationOrganic solvent was concentrated
  3. additionadded water, dilute HCl
  4. additionwas added
  5. stirringunder stirring
  6. filtrationThe reaction mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-7f4be3bdcc0e4a52bfdffa93ced91cef
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

Notizen zur Reaktion

Wird geladen…