Water → N,N'-Dicyclohexylurea

HRID 1943983Notes

Reaction equation

HRID 1943983 reaction equation
[CH:1]1([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:16]>CN(C=O)C>[C:8]([NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:16]

Participants

4

Reactant 2

HCID 962WaterHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

To N-TeocT4 (0.017 g, 17 μmol) in 1 mL dry DMF was added dicyclohexylcarbodiimide (0.004 g, 18 μmol). After stirring for 30 minutes N-dimethyl-4-aminopyridine (0.004 g, 36 μmol) and Gly18 (0.017 g, 17 μmol) were added and the reaction stirred overnight. The cloudy solution was poured into 20 mL H2O and extracted twice with 10 mL CH2Cl2. The aqueous component was acidified to pH 3 with 1 N HCl and chilled to 4° C. The material was isolated by centrifugation and the pellet washed 3 times with 8 mL H2O. The pellet was dried in vacuum to yield dicyclohexylurea and N-TeocT4-Gly18.(SEQ ID NO: 6)

Workup

  1. additionGly18 (0.017 g, 17 μmol) were added
  2. extractionextracted twice with 10 mL CH2Cl2
  3. customThe material was isolated by centrifugation
  4. washthe pellet washed 3 times with 8 mL H2O
  5. customThe pellet was dried in vacuum

Sources & evidence

ORD record
ord-535d1a5f02d945cf9fa140a5776a4ada
Source dataset
uspto-grants-2013_03
Patent number
US08394813B2

Reaction notes

Loading…