2,6-Lutidine → N-{1-[3-(n-butoxycarbonylamino)benzyl] indol-5-ylcarbonyl}-2-methylbenzene sulphonamide

HRID 2081701Notes

Reaction equation

HRID 2081701 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])(=[O:20])=[O:19])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.N1C(C)=CC=CC=1C.Cl[C:40]([O:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:41]>ClCCl>[CH2:43]([O:42][C:40]([NH:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])(=[O:20])=[O:19])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[O:41])[CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 61140Butyl chloroformateHCID 19780416N-[1-(3-aminobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide

Product 1

HCID 19780412N-{1-[3-(n-butoxycarbonylamino)benzyl] indol-5-ylcarbonyl}-2-methylbenzene sulphonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The amine (Example 4) (0.17 g) was dissolved in dichloromethane (5 ml) and 2,6-lutidine (50 μl) and stirred as n-butyl chloroformate (55 μl) was added over 2 minutes. The reaction mixture was stirred for 3 hours, diluted with dichloromethane and washed with 0.5N hydrochloric acid, then water. The organic extract was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with 0-5% ethyl acetate in dichloromethane, yielded N-{1-[3-(n-butoxycarbonylamino)benzyl] indol-5-ylcarbonyl}-2-methylbenzene sulphonamide as a gum.

Workup

  1. additionwas added over 2 minutes
  2. washwashed with 0.5N hydrochloric acid
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography on silica
  8. washeluting with 0-5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-bd8a440856ae4947b90c038c8d4f9600
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

Loading…