1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-4-(N,N-Di-n-pentylcarbamoyl)-1-(N,N-diphenylcarbamoyl)-2-(2-(4-morpholinyl)ethylaminocarbonyl)piperazine

HRID 2226026Notes

Reaction equation

HRID 2226026 reaction equation
[C:1]1([N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[N:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:12][CH:11]2[C:29](O)=[O:30])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[NH2:49][CH2:50][CH2:51][N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>CN(C1C=CN=CC=1)C>[CH2:23]([N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8](=[O:9])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@H:11]([C:29]([NH:49][CH2:50][CH2:51][N:52]2[CH2:57][CH2:56][O:55][CH2:54][CH2:53]2)=[O:30])[CH2:12]1)=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4082852-MorpholinoethylamineHCID 98709141-(N,N-diphenylcarbamoyl)-4-(N,N-di-n-pentylcarbamoyl)piperazine-2-carboxylic acid

Product 1

HCID 54538407(S)-4-(N,N-Di-n-pentylcarbamoyl)-1-(N,N-diphenylcarbamoyl)-2-(2-(4-morpholinyl)ethylaminocarbonyl)piperazineYield 46.5%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

According to the procedure of Example 1, Step E above, 47 mg (0.09 mmole) of 1-(N,N-diphenylcarbamoyl)-4-(N,N-di-n-pentylcarbamoyl)piperazine-2-carboxylic acid, 3 mg (0.02 mmole) of DMAP, 25 mg (0.13 mmole) of EDAC, and 24 mg (0.18 mmole) of 4-(2-aminoethyl)morpholine after purification by flash chromatography on 16 g of silica gel with 100:3CH2Cl2 :MeOH provided 26 mg (46%) of an oil.

Workup

  1. customafter purification by flash chromatography on 16 g of silica gel with 100:3CH2Cl2

Sources & evidence

ORD record
ord-e1da493f1b254e4b9214105d3abcc999
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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