Sodium Hydroxide → HCID 21200250, compound

HRID 1066501Notes

Reaction equation

HRID 1066501 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[C:14]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][N:34]=3)(=[O:32])=[O:31])[N:13]=2)[CH:7]=1.[OH-].[Na+].C(Cl)Cl.CCOC(C)=O>CO>[CH3:19][O:18][C:16]1[C:15]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])=[C:14]([NH:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][N:34]=2)(=[O:32])=[O:31])[N:13]=[C:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[O:5][CH2:4][C:3]([OH:40])=[O:2])[N:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226138Dichloromethane ethylacetateHCID 53666334{3-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenoxy}-acetic acid methyl ester2×

Product 1

HCID 21200250HCID 21200250, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

85 mg of {3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenoxy}-acetic acid methyl ester, product of example 2, dissolved in MeOH (30 ml) were treated at RT with 1N NaOH (0.9 ml) and the solution was stirred for 1 h until the transformation was complete according to TLC analysis (CH2Cl2/EtOAc: 3:1). The reaction mixture was partitioned between 1N HCl and CH2Cl2, the organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue upon triturating with ether provided the desired {3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenoxy}-acetic acid as a white solid. ISN mass spectrum, m/e 551 (M−1 calculated for C26H24N4O8S: 551).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and CH2Cl2
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe residue upon triturating with ether

Sources & evidence

ORD record
ord-778690e5da974e81a54ca5de746623cc
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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