1,1'-Carbonyldiimidazole → HCID 59708795, compound

HRID 1097301Notes

Reaction equation

HRID 1097301 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=O)[CH2:27][CH2:26]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:38]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>ClCCl>[C:41]([O:40][C:38]([N:45]1[CH2:50][CH2:49][N:48]([C:35](=[O:37])[CH2:34][CH2:33][CH2:32][CH2:31][N:28]2[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[CH2:30][CH2:29]2)[CH2:47][CH2:46]1)=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 59708794HCID 59708794, compound

Product 1

HCID 59708795HCID 59708795, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (129 mg, 0.796 mmol) was added to a solution of 5-[4-(4-tert-butoxycarbonylaminobutyl)piperazin-1-yl]pentanoic acid (111) (219 mg, 0.613 mmol) in anhydrous dichloromethane (8 mL) and the mixture was stirred at room temperature for 2 hours. N-Boc piperazine (148 mg, 0.796 mmol) was then added in one portion and the reaction mixture was stirred at room temperature for an additional 16 hours. The mixture was then concentrated under reduced pressure, and the resulting residue was purified by Biotage silica gel column chromatography using methanol/dichloromethane (gradient 0% to 2%) to give 4-{5-[4-(4-tert-butoxycarbonylaminobutyl)piperazin-1-yl]pentanoyl}piperazine-1-carboxylic acid tert-butyl ester 112 as a viscous, yellow oil (309 mg, 96%): 1H NMR (500 MHz, CDCl3) δ 1.44 (s, 9H), 1.48 (s, 9H), 1.55 (m, 6H), 1.66 (m, 2H), 2.35 (m, 8H), 2.48 (m, 6H), 3.11 (m, 2H), 3.40 (m, 2H), 3.44 (m, 4H), 3.58 (m, 2H), 5.30 (br, 1H). m/z (ESI) 526 [C27H51N5O5+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for an additional 16 hours
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customthe resulting residue was purified by Biotage silica gel column chromatography

Sources & evidence

ORD record
ord-b3237dafee7c450e969b43f7562c7c55
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

Loading…