Triethylamine → (4-{[(4-Dipropylamino-butyl)-methanesulfonyl-amino]-methyl}-benzyl)-carbamic acid t-butyl ester

HRID 2080835Notes

Reaction equation

HRID 2080835 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH3:27])[S:37]([CH3:36])(=[O:39])=[O:38])=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

Product 1

HCID 67103854(4-{[(4-Dipropylamino-butyl)-methanesulfonyl-amino]-methyl}-benzyl)-carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (198.3 mg) obtained in Example 23-4 was dissolved in anhydrous dichloromethane (4.0 ml) and added with triethylamine (0.142 ml) and methanesulfonyl chloride (0.060 ml), and the whole was stirred at room temperature for 1 hour. After completion of the reaction, the resultant was washed with water and dried with anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (192.0 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. washthe resultant was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-4b0666bb19d344f3acf2e250704749f9
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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