Dimethylformamide → HCID 178501776, compound

HRID 234132Notes

Reaction equation

HRID 234132 reaction equation
[Na+].[Na+].C([NH:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]([NH:16][CH2:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O-:30])=O)=[C:22]([O:31][CH2:32][C:33]([O-:35])=[O:34])[CH:21]=2)=[O:19])=[O:15])[CH2:10][CH2:9]1)(=O)C.[CH2:36](N(CC)CC)C.[C:43]([C:45]1[CH:53]=[CH:52][C:48]([C:49](Cl)=[O:50])=[CH:47][CH:46]=1)#[N:44].CN(C)[CH:56]=[O:57]>C(Cl)(Cl)Cl>[C:43]([C:45]1[CH:53]=[CH:52][C:48]([C:49]([NH:6][CH2:7][C@H:8]2[CH2:9][CH2:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O:57][CH3:56])=[O:30])=[C:22]([O:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:21]=3)=[O:19])=[O:15])[CH2:12][CH2:13]2)=[O:50])=[CH:47][CH:46]=1)#[N:44]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 178474846HCID 178474846, compound

Product 1

HCID 178501776HCID 178501776, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the solution of 470 mg (0.83 mmole) of the compound prepared in Example 5 (a) in 5 ml of dimethylformamide were added 0.23 ml of triethylamine and 138 mg of 4-cyanobenzoyl chloride, and the mixture was stirred at room temperature for 1 hour. After the reaction mixture was concentrated under reduced pressure, the residue thus obtained was dissolved in chloroform, washed with water and dried over anhydrous magnesium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure. The solid product thus obtained was washed with ether to give 300 mg of dimethyl [[4-[[[trans-4-[(p-cyanobenzoyl)aminomethyl]cyclohexyl]carbonylamino]acetyl]-o-phenylene]dioxy]diacetate (yield, 62%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the inorganic salt was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe solid product thus obtained
  8. washwas washed with ether

Sources & evidence

ORD record
ord-570ef32381d54d5f8d27f9b3ab1c93f4
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

Loading…