Dicyclohexylcarbodiimide → HCID 178524265, compound

HRID 1941085Notes

Reaction equation

HRID 1941085 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]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:2][C:1]([C:4]3[CH:5]=[CH:6][C:7]([B:10]([OH:12])[OH:11])=[CH:8][CH:9]=3)=[O:3])[C:17]=2[N:16]=[N:15]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 178524265HCID 178524265, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 4-carboxy-phenylboronic acid (CPBA, Example 1, 2 g, 0.0121 mol) in N,N-dimethylformamide (DMF) was added 1-hydroxybenzotriazole (HBT, 2.04 g, 0.0151 mol) and N,N'-dicyclohexyl-carbodiimide (DCC, 4.98 g, 0.024 mol) both dissolved in DMF (the total volume was 170 ml DMF). The solution was left to react overnight (approx. 12 hours) under a nitrogen atomosphere and 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 overnight (approx. 12 hours) under a nitrogen atomosphere
  3. filtrationat ambient temperature, and then filtered
  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-213cf27f0ad547f3b3ef20d9dd129e94
Source dataset
uspto-grants-1997_12
Patent number
US05702952

Reaction notes

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