Hydrochloric Acid → 5-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acid

HRID 251702

Reaktionsgleichung

Reaktionsgleichung von HRID 251702
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=3)[NH:19][C:18]2=[O:27])[CH:11]=1.CO.[Li+].[OH-].Cl>O>[F:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:27])[C:17]2=[CH:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:29])=[O:2])=[O:28]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 690347625-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acid methyl ester

Produkt 1

HCID 690319325-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)pentanoic acid methyl ester (396 mg, 1 mmol) and 300 ml of CH3OH were stirred at room temperature while 25 ml of 4 N solution of LiOH in H2O was added. The mixture was stirred for 24 hours at room temperature. The mixture is neutralized with concentrated hydrochloric acid to pH 7 and evaporated under vacuum to remove methanol. The residue was adjusted to pH 3 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (294 mg, 77% yield) as a brown solid. LC-MS (m/z) 383 (M+1).

Aufarbeitung

  1. additionwas added
  2. customevaporated under vacuum
  3. customto remove methanol
  4. filtrationThe solids were collected by vacuum filtration
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-00c51be967a84974a1f6de6447f10fc6
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863315B2

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