Water → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-(propionamidomethyl)pyrrole

HRID 613635Notes

Reaction equation

HRID 613635 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]=2[Cl:34])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:42](Cl)(=[O:45])[CH2:43][CH3:44].O>ClCCl>[Si:17]([O:16][CH2:15][C:10]1[C:9]([Cl:34])=[C:8]([N:4]2[CH:5]=[CH:6][CH:7]=[C:3]2[CH2:2][NH:1][C:42](=[O:45])[CH2:43][CH3:44])[CH:13]=[CH:12][C:11]=1[Cl:14])([C:30]([CH3:31])([CH3:33])[CH3:32])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 183217752-Aminomethyl-1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrrole

Product 1

HCID 183219481-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-(propionamidomethyl)pyrroleYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-aminomethyl-1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]pyrrole (167 mg) and triethylamine (39.8 mg) in dichloromethane (2 ml) was added propionyl chloride (33.4 mg) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature and for 3 hours at ambient temperature. The mixture was poured into water and extracted with chloroform. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 1-(3-tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-(propionamidomethyl)pyrrole (185 mg) as oil.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e6e333c441d4b4c9baf4a668f193289
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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