1,1'-Carbonyldiimidazole → 4-(12-tert-Butoxycarbonylaminododecanoyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 2420753Notes

Reaction equation

HRID 2420753 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl>[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][N:45]([C:20](=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 4428132Boc-12-Ado-OH

Product 1

HCID 672154104-(12-tert-Butoxycarbonylaminododecanoyl)piperazine-1-carboxylic acid tert-butyl esterYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 12-tert-butoxycarbonylaminododecanoic acid (3) (320 mg, 1.01 mmol) and 1,1′-carbonyldiimidazole (181 mg, 1.12 mmol) in anhydrous CH2Cl2 (10 mL) was stirred at room temperature for 2 hours. Then N-tert-butoxycarbonylpiperazine (227.0 mg, 1.22 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 66 hours. After this time, the solvent was removed by rotary evaporation and the resulting residue was purified with Biotage silica gel column chromatography, eluting with 5% to 36% ethyl acetate/hexanes, to afford the desired amide 10 (462.0 mg, 94%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.25 (m, 14H), 1.42 (s, 9H), 1.47 (s, 9H), 1.62 (m, 2H), 2.30 (t, 2H), 3.10 (m, 2H), 3.42 (m, 6H), 3.60 (m, 2H), 4.49 (br, 1H). m/z (ESI) 484 [C26H49N3O5+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 66 hours
  2. customAfter this time, the solvent was removed by rotary evaporation
  3. customthe resulting residue was purified with Biotage silica gel column chromatography
  4. washeluting with 5% to 36% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e7b5f48ba0d94ec29c9ccae3119f0dfc
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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