Hydrochloric Acid → 3-Methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl) isoxazole-5-carboxamido)butanoic acid

HRID 75831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75831
[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[C:4]([O:6]C)=[O:5].O.[OH-].[Li+].Cl>C1COCC1>[CH3:1][CH:2]([CH3:36])[CH:3]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:30][CH:31]=3)=[O:24])=[CH:20][CH:21]=2)[CH:12]=1)=[O:10])[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67352407Methyl 3-methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoxazole-5-carboxamido)butanoate

Produkt 1

HCID 673534913-Methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl) isoxazole-5-carboxamido)butanoic acidAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To Methyl 3-methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoxazole-5-carboxamido)butanoate (250 mg) dissolved in THF (5 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (1 ml) and stirred at RT for 14 h. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over. Na2SO4 and concentrated under reduced pressure to get off white solid which was crystallized from EtOAc to yield 185 mg (76%) white solid. MS (ES+): m/z 491 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ 12.82 (bs, 1H), 9.22 (s, 1H), 9.12 (s, 1H), 8.93 (d, 1H), 7.85 (d, 2H), 7.68 (s, 1H), 7.65 (d, 2H), 7.61 (d, 2H), 7.56 (d, 2H), 4.26 (m, 1H), 2.21 (m, 1H), 0.95 (d, 6H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. customdried over
  4. concentrationNa2SO4 and concentrated under reduced pressure
  5. customto get off white solid which
  6. customwas crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-087fed4df0044aa59dcdaa948153bb64
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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