Dicyclohexylcarbodiimide → HCID 54231837, compound

HRID 1108960Notes

Reaction equation

HRID 1108960 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH2:17]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[C:33]([O:37][C:38]([N:40]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:41][C:42](O)=[O:43])=[O:39])([CH3:36])([CH3:35])[CH3:34].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:33]([O:37][C:38]([N:40]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:41][C:42]([N:30]1[CH2:29][CH2:28][N:27]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:32][CH2:31]1)=[O:43])=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 19377586HCID 19377586, compoundHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycine

Product 1

HCID 54231837HCID 54231837, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.3 g (8.64 mmole) quantity of N,N'-dicyclohexylcarbodiimide was added to 20 ml of a solution of 2.0 g (7.35 mmole) of N-decylpiperazine hydrochloride, 1.9 g (7.56 mmole) of N-t-butoxycarbonylphenylglycine, 1.3 g (15.5 mmole) of sodium hydrogencarbonate and 122 mg (1.0 mmole) of 4-dimethylaminopyridine in anhydrous methylene chloride. The mixture was stirred at room temperature for 12 hours. The precipitated crystals were collected by filtration and washed with methylene chloride. Mother liquor and the washings were combined and concentrated under reduced pressure and the residue was purified by silica gel chromatography (chloroform : methanol =15 : 1), giving 2.8 g (yield: 83 %) of 1-(N-t-butoxycarbonyl-phenylglycyl)-4-decylpiperazine.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with methylene chloride
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (chloroform : methanol =15 : 1)

Sources & evidence

ORD record
ord-b0e4ea46eaad49809a7f950ba6b27acc
Source dataset
uspto-grants-1994_06
Patent number
US05318970

Reaction notes

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