1,1'-Carbonyldiimidazole → 4-(11-tert-Butoxycarbonylaminoundecanoyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 2420744Notes

Reaction equation

HRID 2420744 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][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>O1CCCC1>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][N:44]([C:31](=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 422929011-((tert-Butoxycarbonyl)amino)undecanoic acid

Product 1

HCID 672149744-(11-tert-Butoxycarbonylaminoundecanoyl)piperazine-1-carboxylic acid tert-butyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,1′-Carbonyldiimidazole (118 mg, 0.73 mmol) was added to a solution of acid 3 (200 mg, 0.66 mmol) in tetrahydrofuran (5 mL) and the mixture stirred for 4 hours. A solution of N-tert-butoxycarbonylpiperazine (148 mg, 0.79 mmol) in tetrahydrofuran (2 mL) was added and the reaction stirred for an additional 14 hours at room temperature. The solvent was then removed under vacuum and the residual oil purified by column chromatography (silica gel, gradient 99:1 to 95:5 dichloromethane/methanol, v/v) to afford 7 (204 mg, 66%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.27 (m, 12H), 1.41-1.51 (m, 21H), 1.56-1.66 (m, 5H), 2.32 (t, 2H, J=7.5 Hz), 3.08-3.11 (m, 2H), 3.38-3.41 (m, 2H), 3.56-3.59 (m, 2H), 4.51 (br, 1H); m/z (ESI) 470 [C25H47N3O5+H]+.

Workup

  1. stirringthe reaction stirred for an additional 14 hours at room temperature
  2. customThe solvent was then removed under vacuum
  3. customthe residual oil purified by column chromatography (silica gel, gradient 99:1 to 95:5 dichloromethane/methanol, v/v)

Sources & evidence

ORD record
ord-11bca81605924f17904ed6c341984f97
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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