benzyl 3-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid benzyl ester → 3-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid

HRID 2406147Notes

Reaction equation

HRID 2406147 reaction equation
C([O:8][C:9](=[O:42])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16](=[O:34])(=[O:33])[NH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24](=[O:32])[N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[O:21])[C:11]=1CC1C=CC=CC=1)C1C=CC=CC=1>C(OC(C)C)(=O)C.[Pd]>[CH2:29]([N:25]([CH2:26][CH2:27][CH3:28])[C:24]([CH2:23][O:22][C:20]([CH2:19][CH2:18][NH:17][S:16]([C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:9]([OH:42])=[O:8])(=[O:34])=[O:33])=[O:21])=[O:32])[CH2:30][CH3:31]

Participants

4

Reactant 1

HCID 66797488benzyl 3-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid benzyl ester

Product 1

HCID 667975393-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7915Isopropyl AcetateSolvent

Procedure

A solution of benzyl 3-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid benzyl ester (5 g, 33.25 mmol) in isopropyl acetate (82 ml) was treated with 10% Pd/C (0.84 g, 50% wet), and stirred under H2 (3 atm) overnight. The catalyst was removed by filtration. To the filtrate was added 10% Pd/C (1.68 g, 50% wet), and the reaction stirred under H2 (3 atm) for 18 h. The catalyst was removed by filtration and further 10% Pd/C (1.68 g, 50% wet) was added and the reaction stirred under H2 (1 atm) for 18 h. The catalyst was removed by filtration and washed with isopropyl acetate (20 ml). The combined filtrates were concentrated in vacuo and heptane was added to the solution and stirred at RT for 2 hr then −2° C. for 4 h. The solid which formed was collected by filtration and dried under vacuum at 40° C. to afford the title compound; LC-MS; 415.1 [M+H]+, Method (i).

Workup

  1. customThe catalyst was removed by filtration
  2. additionTo the filtrate was added 10% Pd/C (1.68 g, 50% wet)
  3. stirringthe reaction stirred under H2 (3 atm) for 18 h
  4. customThe catalyst was removed by filtration and further 10% Pd/C (1.68 g, 50% wet)
  5. additionwas added
  6. stirringthe reaction stirred under H2 (1 atm) for 18 h
  7. customThe catalyst was removed by filtration
  8. washwashed with isopropyl acetate (20 ml)
  9. concentrationThe combined filtrates were concentrated in vacuo and heptane
  10. additionwas added to the solution
  11. stirringstirred at RT for 2 hr
  12. wait−2° C. for 4 h
  13. customThe solid which formed
  14. filtrationwas collected by filtration
  15. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-4aeb31e909ce40249cbc3e5c2f5dd0bf
Source dataset
uspto-grants-2014_08
Patent number
US08809340B2

Reaction notes

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