1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-2-(2-(N-Benzyl-N-methylamino)-N-(methyl)ethylaminocarbonyl)-4-(N,N-di-n-pentylcarbamoyl)-1-(N,N-diphenylcarbamoyl)piperazine

HRID 2226027Notes

Reaction equation

HRID 2226027 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]([OH:31])=O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:59]([N:66]([CH3:71])[CH2:67][CH2:68][NH:69][CH3:70])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[CH2:59]([N:66]([CH2:67][CH2:68][N:69]([CH3:70])[C:29]([C@@H:11]1[CH2:12][N:13]([C:16](=[O:28])[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:14][CH2:15][N:10]1[C:8](=[O:9])[N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:31])[CH3:71])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66016N-Benzyl-N,N'-dimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 98709141-(N,N-diphenylcarbamoyl)-4-(N,N-di-n-pentylcarbamoyl)piperazine-2-carboxylic acid

Product 1

HCID 18654560(S)-2-(2-(N-Benzyl-N-methylamino)-N-(methyl)ethylaminocarbonyl)-4-(N,N-di-n-pentylcarbamoyl)-1-(N,N-diphenylcarbamoyl)piperazineYield 78%

Procedure

According to the procedure of Example 1, Step E above, 48 mg (0.094 sole) of 1-(N,N-diphenylcarbamoyl)-4-(N,N-di-n-pentylcarbamoyl)piperazine-2carboxylic acid, 14 mg (0.104 mmole) of HOBt, 25 mg (0.132 mmole) of EDAC, and 34 mg (0.19 mmole) of N-benzyl-N-methyl-N'-methylethylenediamine after purification by flash chromatography on 16 g of silica gel eluting with 400 mL of 100:4 CH2Cl2 :MeOH provided 49 mg (78%) of an oil.

Workup

  1. customafter purification by flash chromatography on 16 g of silica gel eluting with 400 mL of 100:4 CH2Cl2

Sources & evidence

ORD record
ord-7c308527a2504e3ab3bb25a61763a8f7
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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