1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[2-(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetylsulfamoyl]-butyric acid methyl ester

HRID 1445912Notes

Reaction equation

HRID 1445912 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][C:19](O)=[O:20])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][S:29](=[O:32])(=[O:31])[NH2:30].CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][S:29](=[O:31])(=[O:32])[NH:30][C:19](=[O:20])[CH2:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([CH3:22])[N:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10511613Methyl 4-sulfamoylbutanoateHCID 18461534(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid

Product 1

HCID 685477134-[2-(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetylsulfamoyl]-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid (5) (0.189 g, 0.64 mmole) in dichloromethane (15 mL), 4-sulfamoyl-butyric acid methyl ester (0.232 g, 1.28 mmole), EDCI (0.122 g, 0.64 mmole) and DMAP (0.078 g, 0.64 mmole) were added. The mixture was stirred at room temperature for 18 h. The dichloromethane was evaporated to half of the original volume and the mixture was washed with water (2×10 mL). The organic layer was separated and evaporated. The residue was purified by column chromatography (10:1 CHCl3:MeOH) to afford intermediate (6) as a solid. Yield: 0.15 g, 51%

Workup

  1. customThe dichloromethane was evaporated to half of the original volume
  2. washthe mixture was washed with water (2×10 mL)
  3. customThe organic layer was separated
  4. customevaporated
  5. customThe residue was purified by column chromatography (10:1 CHCl3:MeOH)

Sources & evidence

ORD record
ord-695312058b34417980a41988dd6d0801
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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