Sodium Hydroxide → HCID 70228201, compound

HRID 1596410Notes

Reaction equation

HRID 1596410 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=1)[CH:7]([N:10]1[C:18]2[C:17]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[N:29][CH:30]=4)=[CH:22][C:16]=3[CH2:15][CH2:14][C:13]=2[C:12]([C:31]([OH:33])=[O:32])=[N:11]1)[CH2:8][CH3:9])[CH3:2].[OH-].[Na+:38]>O>[Na+:38].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=1)[CH:7]([N:10]1[C:18]2[C:17]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[N:29][CH:30]=4)=[CH:22][C:16]=3[CH2:15][CH2:14][C:13]=2[C:12]([C:31]([O-:33])=[O:32])=[N:11]1)[CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9935039219705-77-8

Product 1

HCID 70228201HCID 70228201, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4,5-dihydro-1-(3-ethoxy-α-ethylbenzyl)-7-(5-pyrimidinylmethoxy)-[1H]-benz[g]indazole-3-carboxylic acid (600 mg, 1.23 m mol) obtained in Example 34 was suspended in water (20 ml) and dissolved therein by the addition of 1 N sodium hydroxide (2 ml). This solution was subjected to column chromatography using a CHP 20P resin (20 ml; manufactured by Mitsubishi Chemical Co., Ltd.), and eluted successively with water and 50% ethanol-water. After the 50% ethanol-water fraction was concentrated under reduced pressure, the residue was dissolved in water (30 ml) and this solution was concentrated again under reduced pressure. Thereafter, the residue was dissolved in water (15 ml) and freeze-dried to obtain the desired compound (500 mg, 80%) as a colorless powder.

Workup

  1. dissolutiondissolved
  2. washeluted successively with water and 50% ethanol-water
  3. concentrationAfter the 50% ethanol-water fraction was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in water (30 ml)
  5. concentrationthis solution was concentrated again under reduced pressure
  6. dissolutionThereafter, the residue was dissolved in water (15 ml)
  7. customfreeze-dried

Sources & evidence

ORD record
ord-ea6627a7fa92410791c96fe45329d51b
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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