Dibenzylamine → HCID 22415064, compound

HRID 1721391Notes

Reaction equation

HRID 1721391 reaction equation
C([CH:4]([S:8]([O:11][C:12]1[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][C:15]([CH:21]([CH3:23])[CH3:22])=[CH:14][CH:13]=1)(=[O:10])=[O:9])[C:5](O)=[O:6])(C)C.[CH2:24]([NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH:39]1(N=C=NC2CCCCC2)[CH2:44]CCC[CH2:40]1>C(Cl)Cl>[CH2:32]([N:31]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:5]([CH2:4][S:8]([O:11][C:12]1[C:17]([CH:18]([CH3:19])[CH3:20])=[CH:16][C:15]([CH:21]([CH3:23])[CH3:22])=[CH:14][C:13]=1[CH:39]([CH3:44])[CH3:40])(=[O:10])=[O:9])=[O:6])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 10868DicyclohexylcarbodiimideHCID 86749451HCID 86749451, compound

Product 1

HCID 22415064HCID 22415064, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2,4,6-triisopropylphenoxysulfonyl acetic acid (1.0 g, 2.92 mM) in 15 mL of methylene chloride at 0° C. was added a solution of dibenzylamine (0.59 g, 2.92 mM) and dicyclohexylcarbodiimide (0.62 g, 3 mM) in 10 mL of methylene chloride. The reaction mixture was stirred 1 hour at 0° C., warmed to 24° C., and stirred at that temperature for 12 hours. The reaction mixture was filtered to remove the solid precipitate. The filtrate was concentrated to an oil by evaporation of the solvent under reduced pressure. The oil was purified by chromatography over a silica gel column, eluting with hexane:ethyl acetate (1:1 v/v). The fractions showed by thin layer chromatography to contain the major component were combined and the solvent was removed by evaporation under reduced pressure to provide 0.5 g (76%) of 2,4,6-triisopropylphenyl N,N-dibenzylcarbamoylmethyl sulfonate, mp 107°-110° C.

Workup

  1. temperaturewarmed to 24° C.
  2. stirringstirred at that temperature for 12 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove the solid precipitate
  5. concentrationThe filtrate was concentrated to an oil by evaporation of the solvent under reduced pressure
  6. customThe oil was purified by chromatography over a silica gel column
  7. washeluting with hexane:ethyl acetate (1:1 v/v)
  8. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4e63e8f5cde244cf87a28e29f096ca66
Source dataset
uspto-grants-1996_04
Patent number
US05510379

Reaction notes

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