1,1'-Carbonyldiimidazole → (S)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester

HRID 1887191Notes

Reaction equation

HRID 1887191 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:24][O:25][C:26](=[O:32])[CH2:27][C@@H:28]([NH2:31])[CH2:29][CH3:30]>N1C=CC=CC=1>[CH3:24][O:25][C:26](=[O:32])[CH2:27][C@@H:28]([NH:31][C:8]([C:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 738363-Aminopicolinic acidHCID 51358236methyl (3S)-3-aminopentanoate hydrochloride

Product 1

HCID 67503115(S)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 321 mg of 3-aminopyridine-2-carboxylic acid in pyridine (5.0 mL) is added 377 mg of 1,1′-carbonyldiimidazole and the mixture is stirred for 2 h at room temperature. The resulting mixture is treated with 300 mg of (S)-3-aminopentanoic acid methyl ester hydrochloride and the mixture is stirred for 16 h at room temperature. Then the solvent is removed under vacuum and the residue is purified by flash chromatography on silica gel to give 250 mg (56%) of (S)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester.

Workup

  1. stirringthe mixture is stirred for 16 h at room temperature
  2. customThen the solvent is removed under vacuum
  3. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9da47911eac34ad88e2cbf809d4bb843
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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