Sodium Hydroxide → 4-{[(3-Chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylic acid

HRID 852615Notes

Reaction equation

HRID 852615 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8](S(CCCCl)(=O)=O)[C:9]1[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:22][CH3:23])(=[O:7])=[O:6].[OH-].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:22][CH3:23])(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69357512Methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylate

Product 1

HCID 693571504-{[(3-Chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylate (D236) (1.8 g, 3.6 mmol, 1 equiv) in MeOH (100 ml) was added a 2N aqueous NaOH solution (20 ml, 40 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 to give 4-{[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylic acid (D240) (930 mg, 75%) as a brown oil which was used in the next step without further purification.

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

Sources & evidence

ORD record
ord-14b08453c6cb47548d0bc9c2e928fc29
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…