Dicyclohexylcarbodiimide → HCID 10124616, compound

HRID 507795Notes

Reaction equation

HRID 507795 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23].[CH3:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]2[CH:36]=[C:35]([CH2:37][CH2:38][CH2:39][C:40](O)=[O:41])[CH:34]=[CH:33][N:32]=2)[CH:26]=1>ClCCl>[C:21]1(=[O:22])[N:17]([O:16][C:40](=[O:41])[CH2:39][CH2:38][CH2:37][C:35]2[CH:34]=[CH:33][N:32]=[C:31]([C:27]3[CH:26]=[C:25]([CH3:24])[CH:30]=[CH:29][N:28]=3)[CH:36]=2)[C:18](=[O:23])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 143810894-(4'-Methyl[2,2'-bipyridin]-4-yl)butanoic acid

Product 1

HCID 10124616HCID 10124616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

More specifically, with reference to the reaction scheme I ,4-(4′-methyl-[2,2′]bipyridinyl-4-yl)-butyric acid succinimidyl ester was obtained according to step (5) as follows. 27 mg of DCC (0.129 mmol) and 14 mg N-hydroxysuccinimide (0.129 mmol) were added to 30 mg (0.117 mmol) of 4-(4′-methyl-[2,2′]bipyridinyl-4-yl)-butyric acid (prepared as schematically illustrated by steps (1)-(4) of the reaction scheme I, according to the published procedure in Della Ciana et al., JOC 1989, 54, 1731-1725) in dichloromethane and stirred at room temperature for 2 hours. After 2 hours, the reaction mixture was filtered and concentrated in vacuo. The pure final 4-(4′-methyl-[2,2′]bipyridinyl-4-yl)-butyric acid succinimidyl ester was obtained as a clear oil after column chromatography (SiO2, EtOAc, Hex). 1H NMR: 8.55 (dd, 4H), 8.26 (d, 2H), 7.21 (d, 2H), 2.86 (m, 6H), 2.68 (t, 2H), 2.46 (s, 3H), 2.171 (t, 2H). ESI-MS: m/z=354.

Workup

  1. customprepared
  2. customas schematically illustrated by steps (1)-(4) of the reaction scheme I
  3. waitAfter 2 hours
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56c99c173cd04d93b4dea192fc6136c5
Source dataset
uspto-grants-2010_08
Patent number
US07786298B2

Reaction notes

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