Dimethylformamide → HCID 19611486, compound

HRID 1602509Notes

Reaction equation

HRID 1602509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:42])=[C:18]([CH:41]=2)[NH:19][C:20](=[O:40])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[S:30][C:31]4[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=4[N:33]=3)[CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:50][C:51]([O:53]CC)=[O:52].CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:42][CH2:50][C:51]([OH:53])=[O:52])=[C:18]([NH:19][C:20](=[O:40])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]4[S:30][C:31]5[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=5[N:33]=4)[CH:22]=3)[CH:41]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 19611308HCID 19611308, compound

Product 1

HCID 19611486HCID 19611486, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-hydroxy-3-(6-methoxy-2-benzothiazolylmethoxy)benzanilide (301 mg, 0.48 mmol), potassium carbonate (135 mg, 0.98 mmol), ethyl bromoacetate (81 mg, 0.49 mmol) and dimethylformamide (5 ml) was stirred at room temperature for 12 hours. Water was added to the reaction solution and the product formed was extracted with ethyl acetate. The extract was washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Tetrahydrofuran (2 ml), methanol (1 ml) and 1 N sodium hydroxide were added to the resulting residue and the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated, and water was added to the resulting residue, and the mixture was adjusted to pH 3 with 10% citric acid aqueous solution. Thereafter, the solid material formed was collected by filtration and washed with acetonitrile to give 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[(6-methoxy-2-benzothiazolyl)methoxy]benzoylamino]phenoxyacetic acid (145 mg, 0.21 mmol, 44%).

Workup

  1. customthe product formed
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water and brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTetrahydrofuran (2 ml), methanol (1 ml) and 1 N sodium hydroxide were added to the resulting residue
  7. stirringthe mixture was stirred at room temperature for 12 hours
  8. concentrationThe reaction solution was concentrated
  9. additionwater was added to the resulting residue
  10. customThereafter, the solid material formed
  11. filtrationwas collected by filtration
  12. washwashed with acetonitrile

Sources & evidence

ORD record
ord-a30b859d9f594238ba7d1dde5c4b0a55
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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