Dicyclohexylcarbodiimide → HCID 18454700, compound

HRID 1271643Notes

Reaction equation

HRID 1271643 reaction equation
C([O:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=1)(C)(C)C.C1CCC([N:25]=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[OH-].[NH4+]>CN(C=O)C>[C:14]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[OH:13])[C:6]([NH2:25])=[O:5])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 86036715HCID 86036715, compound

Product 1

HCID 18454700HCID 18454700, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 47E (800 mg, 4.1 mmol), DCC (856 mg, 5.4 mmol), and HOBt (540 mg, 5.4 mmol) were mixed in DMF (10 mL). Ammonium hydroxide (28%, 22 mL) was added to the mixture at 0° C. The reaction was stirred over night and purified by silica gel chromatography (70% -90% EtOAc/Hexane) to provide the title compound (700 mg, 87.5%). MS (DCI) m/z 194 (M+H)+.

Workup

  1. custompurified by silica gel chromatography (70% -90% EtOAc/Hexane)

Sources & evidence

ORD record
ord-078e965e7bb1477990f72d4b09427895
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Reaction notes

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