Hydrochloric Acid → 8-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)octanoic acid

HRID 251707Notes

Reaction equation

HRID 251707 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:31])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=3)[NH:22][C:21]2=[O:30])[CH:14]=1.CO.[Li+].[OH-].Cl>O>[F:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:30])[C:20]2=[CH:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 690362158-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)octanoic acid methyl ester

Product 1

HCID 690357058-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)octanoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)octanoic acid methyl ester (438 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 (305 mg, 72% yield) as a brown solid. LC-MS (m/z) 425 (M+1).

Workup

  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

Sources & evidence

ORD record
ord-64511d85b62848d38cb78e4fa8535b57
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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