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

HRID 75852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75852
[CH3:1][CH:2]([CH3:38])[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](=[O:37])[C:24](=[O:36])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)=[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]([CH3:38])[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](=[O:37])[C:24](=[O:36])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=3)=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67353582Methyl 3-methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino) acetamido)phenyl)isoxazole-5-carboxamido)butanoate

Produkt 1

HCID 673522193-Methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino) acetamido)phenyl)isoxazole-5-carboxamido)butanoic acidAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To methyl 3-methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino)acetamido) phenyl)isoxazole-5-carboxamido)butanoate (100 mg) in THF (2 ml) 1 M aqueous solution of Lithium hydroxide monohydrate (0.375 ml) was added and reaction mixture was stirred at RT for 6 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was collected and dried over Na2SO4 and concentrated to obtain off white solid, which was crystallized from EtOAc to yield 22 mg (22%) of the title compound as white solid. MS (ES+): m/z 519 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 11.24 (s, 1H), 11.13 (s, 1H), 9.01 (d, 1H), 8.35 (dd, 1H), 8.16 (dd, 1H), 8.06 (d, 2H), 7.96 (d, 2H), 7.73 (s, 1H), 7.64 (m, 1H), 7.54 (dd, 1H), 4.28 (m, 1H), 2.23 (m, 1H), 0.98 (d, 6H).

Aufarbeitung

  1. customreaction mixture
  2. extractionextracted with EtOAc
  3. customOrganic layer was collected
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain off white solid, which
  7. customwas crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-40b056e5d68e4f66b7f46f43614f10ca
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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