Sodium Hydroxide → HCID 69359492, compound

HRID 852583Notes

Reaction equation

HRID 852583 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8](S(CCCCl)(=O)=O)[C:9]1[C:10]([F:22])=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[C:12]([O:14]C)=[O:13])(=[O:7])=[O:6].[OH-].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[C:10]([F:22])=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[C:12]([OH:14])=[O:13])(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69357394HCID 69357394, compound

Product 1

HCID 69359492HCID 69359492, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude methyl 3-{bis[(3-chloropropyl)sulfonyl]amino}-2-fluoro-5-nitrobenzoate (D141) (900 mg, 1.81 mmol, 1 equiv) in MeOH (25 ml) was added a 2N aqueous NaOH solution (15 ml, 30 mmol, excess) and the resulting mixture was stirred for 1 h. Most of MeOH was removed in vacuo and the residue partitioned between AcOEt and a 2N aqueous HCl solution. The two layers were separated and the aqueous phase was dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O/iso-hexane to give 3-{[(3-chloropropyl)sulfonyl]amino}-2-fluoro-5-nitrobenzoic acid (D143) (600 mg, 97%) as a light tan solid which was used in the next step without further purification. No molecular ion, RT=3.05 min.

Workup

  1. customMost of MeOH was removed in vacuo
  2. customthe residue partitioned between AcOEt
  3. customThe two layers were separated
  4. dry with materialthe aqueous phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with Et2O/iso-hexane

Sources & evidence

ORD record
ord-25e43146583547a2aff47b6a7c673997
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…