1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-1-(N-(3-chlorophenyl)-N-phenylcarbamoyl)-2-(2-(N-methyl-N-(2-methoxybenzyl)amino)ethylaminocarbonyl)-4-(N,N-di-n-pentylcarbamoyl) piperazine

HRID 2226029Notes

Reaction equation

HRID 2226029 reaction equation
[CH2:1]([N:6]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:30])[N:16]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([C:31](O)=[O:32])[CH2:10]1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:60][O:61][C:62]1[CH:73]=[CH:72][CH:71]=[CH:70][C:63]=1[CH2:64][N:65]([CH3:69])[CH2:66][CH2:67][NH2:68]>>[Cl:29][C:25]1[CH:24]=[C:23]([N:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:7](=[O:8])[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:10][C@H:11]2[C:31]([NH:68][CH2:67][CH2:66][N:65]([CH3:69])[CH2:64][C:63]2[CH:70]=[CH:71][CH:72]=[CH:73][C:62]=2[O:61][CH3:60])=[O:32])=[O:30])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6484249N1-(2-methoxybenzyl)-N1-methylethane-1,2-diamineHCID 228506671-[3-chlorophenyl(phenyl)carbamoyl]-4-dipentylcarbamoyl-(2S)-hexahydro-2-pyrazinecarboxylic acid

Product 1

HCID 18654559(S)-1-(N-(3-chlorophenyl)-N-phenylcarbamoyl)-2-(2-(N-methyl-N-(2-methoxybenzyl)amino)ethylaminocarbonyl)-4-(N,N-di-n-pentylcarbamoyl) piperazineYield 84.5%

Procedure

According to the procedure of Example 1, Step E above, 43 mg (0.079 mmole) of (S)-4-(dipentylcarbamoyl)-1-(N-(3-chlorophenyl)-N-phenylcarbamoyl)piperazine-2-carboxylic acid, 12 mg (0.087 mmole) of HOBt, 21 mg (0.111 mmole) of EDAC, and 31 mg (0.158 mmole) of N-(2-methoxybenzyl)-N-methylethylenediamine after purification by flash chromatography on 16 g of silica gel eluting with 100:4 CH2Cl2 :methanol provided 48 mg (84%) of an oil.

Workup

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

Sources & evidence

ORD record
ord-84e404fe6aae4625a9527b16bca1fc0f
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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