1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → HCID 69152279, compound

HRID 1744075Notes

Reaction equation

HRID 1744075 reaction equation
[OH:1][C:2]([CH3:12])([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH:13]1[CH:18]=[C:17]2[C:19]([N:21]([CH2:24][C:25](O)=[O:26])[C:22](=[O:23])[C:16]2=[CH:15][CH:14]=1)=[O:20].CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>CN(C1C=CN=CC=1)C.ClCCl>[O:20]=[C:19]1[C:17]2[C:16](=[CH:15][CH:14]=[CH:13][CH:18]=2)[C:22](=[O:23])[N:21]1[CH2:24][C:25]([O:1][C:2]([CH3:12])([CH3:11])[C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:26]

Participants

6

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 20825N-PhthaloylglycineHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-one

Product 1

HCID 69152279HCID 69152279, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-hydroxy-2-methylpropiophenone (2.0 g, 12.2 mmol), N-phthaloylglycine (2.7 g, 13.2 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (10.3 g, 24.3 mmol) and DMAP (0.34 g, 2.8 mmol) was dissolved in dichloromethane (100 mL) and stirred 5 days at room temperature. The mixture was diluted with dichloromethane and washed with 1 M HCl (2×), saturated NaHCO3 and brine, then filtered through cotton and concentrated to give 1,1-dimethyl-2-oxo-2-phenylethyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetate.

Workup

  1. washwashed with 1 M HCl (2×), saturated NaHCO3 and brine
  2. filtrationfiltered through cotton
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-73173afbf87c4d7b941423a77c3b697c
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…