Hydrochloric Acid → 8-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-octanoic acid

HRID 251679Notes

Reaction equation

HRID 251679 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:18]([CH3:19])=[C:17]([CH:20]=[N:21][N:22]=[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([F:32])[CH:30]=3)[NH:25][C:24]2=[O:33])[NH:16][C:15]=1[CH3:34])=[O:13].CO.[Li+].[OH-].Cl>O>[F:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:33])[C:23]2=[N:22][N:21]=[CH:20][C:17]1[NH:16][C:15]([CH3:34])=[C:14]([C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[O:13])[C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 1363879718-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-octanoic acid methyl ester

Product 1

HCID 1363879728-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-octanoic acidYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-octanoic acid methyl ester (483 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 (159 mg, 34% yield) as a red solid. LC-MS (m/z) 470 (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-c4e4b190b15844d89bc3c390a90ea5ba
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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