Ethyl 2-[4-(aminomethyl)phenyl]propanoate → ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate

HRID 1428798Notes

Reaction equation

HRID 1428798 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9](N1C=CC(=[N+](C)C)C=C1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:24]=1>ClCCl.O>[C:1]([O:5][C:6]([NH:8][S:9]([NH:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][CH:28]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 71019413Ethyl 2-[4-(aminomethyl)phenyl]propanoateHCID 178482963HCID 178482963, compound

Product 1

HCID 86680233ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoateYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-(1-(tert-butoxycarbonyl)sulfamoyl)pyridine-4(1H)-ylidene)-N-methylmethanaminium (A) (5.81 g, 19.32 mmol) was added to a suspension of ethyl 2-(4-(aminomethyl)phenyl)propanoate (4.0 g, 19.32 mmol) in dichloromethane (40 mL) at room temperature and stirred for 16 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×75 mL). Combined organic layer was washed with water (50 mL), brine (50 mL), dried over sodium sulfate and concentrated to get crude compound, which was purified by column chromatography (silica gel; 100-200 mesh). The product eluted with 20% ethyl acetate in pet ether to yielded ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate (3.8 g, 51%) as pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washCombined organic layer was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto get crude compound, which
  6. customwas purified by column chromatography (silica gel; 100-200 mesh)
  7. washThe product eluted with 20% ethyl acetate in pet ether

Sources & evidence

ORD record
ord-0b88f19b5175482ba1ff2042b21897eb
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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