Dichloromethane → HCID 15230999, compound

HRID 1780945Notes

Reaction equation

HRID 1780945 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].O[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].ClCCl.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:15]1(=[O:20])[N:14]([O:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([B:10]([OH:12])[OH:11])=[CH:8][CH:9]=2)=[O:3])[C:18](=[O:19])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 15230999HCID 15230999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Carboxyphenyl-boronic acid (CPBA, Example 1, 0.25 g, 1.51 mmol) and N-hydroxysuccinimide (0.26 g, 2.26 mmol) were dissolved in 8.5 ml DMF using a magnetic stirrer. 20 ml of dichloromethane (CH2Cl2) was then added, and the solution was stirred for 10 minutes. N,N'-dicyclohexyl-carbodiimide (DCC, 0.93 g, 4.52 mmol) in 3 ml CH2Cl was then added. The solution was left to react under a nitrogen atmosphere overnight (approx. 12 hours) at ambient temperature, and then filtered to remove the insoluble urea byproduct (DCU). The title compound was used in subsequent reactions without further purification.

Workup

  1. waitThe solution was left
  2. customto react under a nitrogen atmosphere overnight (approx. 12 hours) at ambient temperature
  3. filtrationfiltered
  4. customto remove the insoluble urea byproduct (DCU)
  5. customThe title compound was used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-6b6e2b7980b642d68dd1b77edd6c47e4
Source dataset
uspto-grants-1997_05
Patent number
US05631364

Reaction notes

Loading…