Water → 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid

HRID 1025572Notes

Reaction equation

HRID 1025572 reaction equation
O.C[O:3][C:4]([C:6]1[N:7]([CH3:34])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N:17]3[N:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:23]=4)[C:18]3=[O:31])[C:12]=2[CH2:32][OH:33])=[CH:9][CH:10]=1)=[O:5].[OH-].[Na+]>O1CCOCC1>[C:27]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:31])[N:17]([C:13]1[C:12]([CH2:32][OH:33])=[C:11]([C:8]3[N:7]([CH3:34])[C:6]([C:4]([OH:5])=[O:3])=[CH:10][CH:9]=3)[CH:16]=[CH:15][CH:14]=1)[N:26]=[CH:25]2)([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 710085895-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 710086185-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Water (5 mL) was added to a solution of 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (150 mg, 0.337 mmol) in dioxane (5 mL). The mixture was stirred for 5 min and NaOH (40 mg) was added. The reaction mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was extracted with diethyl ether (5 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid (113 mg, yield 78%) as a yellow solid. LC-MS calcd for C25H25N3O4 (m/e) 431.18, obsd 885 [2M+23]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionThe residue was extracted with diethyl ether (5 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c6e996cd31848e5a442736bed54411c
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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