Lithium iodide → 3-(2-tert-Butoxycarbonyl-ethylsulfamoyl)-benzoic acid

HRID 2170111Notes

Reaction equation

HRID 2170111 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10](=[O:22])(=[O:21])[NH:11][CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=1.[I-].[Li+]>N1C=CC=CC=1>[C:17]([O:16][C:14]([CH2:13][CH2:12][NH:11][S:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:23])=[O:2])(=[O:22])=[O:21])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 667978353-(2-tert-Butoxycarbonyl-ethylsulfamoyl)-benzoic acid methyl ester

Product 1

HCID 667975563-(2-tert-Butoxycarbonyl-ethylsulfamoyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(2-tert-Butoxycarbonyl-ethylsulfamoyl)-benzoic acid methyl ester (step 1) (5.0 g, 14.56 mmol) and lithium iodide (2.53 g, 18.93 mmol) in pyridine (60 ml) was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo, diluted with DCM (60 ml) and poured into 1.5N HCl (60 ml). The aqueous phase was separated and extracted with DCM (6×60 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The crude residue was purified using an Isolute® PE-AX 10 g cartridge (anion exchange column), eluting with MeOH (200 ml) and then a 1:1 mixture of MeOH/AcOH (200 ml) to afford the title compound as white crystals; 1H NMR (400 MHz, CDCl3) δ 8.63 (1H, s), 8.32(1H, d), 8.14(1H, d), 7.68 (1H, t), 5.63 (1H, t), 3.22 (2H, m), 2.51(2H, t), 1.43 (9H, s).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with DCM (60 ml)
  4. additionpoured into 1.5N HCl (60 ml)
  5. customThe aqueous phase was separated
  6. extractionextracted with DCM (6×60 ml)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified
  10. washeluting with MeOH (200 ml)
  11. additiona 1:1 mixture of MeOH/AcOH (200 ml)

Sources & evidence

ORD record
ord-d913a0001d4b431dac2a7890116c478f
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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