tert-butyl N-(4-aminobutyl)carbamate → {4-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzenesulfonylamino]-butyl}-carbamic acid t-butyl ester

HRID 348702Notes

Reaction equation

HRID 348702 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.[C:30]([O:34][C:35](=[O:42])[NH:36][CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])([CH3:33])([CH3:32])[CH3:31]>C(Cl)(Cl)Cl>[C:30]([O:34][C:35](=[O:42])[NH:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[CH:14][CH:15]=1)(=[O:21])=[O:20])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8471TriethylamineHCID 210844074-[(1,3-Dioxoisoindolin-2-yl)methyl]-1-benzenesulfonyl Chloride

Product 1

HCID 66941808{4-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzenesulfonylamino]-butyl}-carbamic acid t-butyl esterYield 69.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound (1.4396 g) obtained in Example 24-2 was dissolved in anhydrous chloroform (28 ml) and then added with triethylamine (0.689 ml), followed by ice-cooling. Then, the solution was added with (4-aminobutyl)-carbamic acid t-butyl ester (852.9 mg) and stirred at room temperature for 2.5 hours. After the reaction, the solution was washed with water and dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (1.4440 g) as a white solid.

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. washthe solution was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-f42391abe4fe4fe99d16430b5ab2cf0f
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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