Hydrochloric Acid → HCID 67353694, Verbindung

HRID 75818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75818
C[O:2][C:3](=[O:33])[CH:4]([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][CH:29]=[CH:28][C:27]=3[F:32])=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-].Cl>C1COCC1>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:23](=[O:24])[NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:12]=[C:11]([C:9]([NH:8][CH:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:33])=[O:2])=[O:10])[O:15][N:14]=2)=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 673524222-[(3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester

Produkt 1

HCID 67353694HCID 67353694, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-[(3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester (800 mg) was dissolved in THF (20 ml). 1M aqueous LiOH solution (3.52 ml) was added 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 490 mg (63%) white solid. MS (ES+): m/z 441 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 12.83 (bs, 1H), 9.34 (s, 1H), 8.95 (d, 1H), 8.63 (s, 1H), 8.13 (m, 1H), 7.85 (d, 2H), 7.68 (s, 1H), 7.62 (d, 2H), 7.24 (m, 1H), 7.14 (m, 1H), 7.02 (m, 1H), 4.26 (m, 1H), 2.21 (m, 1H), 0.95 (dd, 6H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get off white solid which
  6. customwas crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e01872e5c2c04eb2b140933f6eb132e3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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