1,1'-Carbonyldiimidazole → HCID 67502797, compound

HRID 1887198Notes

Reaction equation

HRID 1887198 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.[C:24]([O:28][C:29](=[O:34])[C@@H:30]([NH2:33])[CH2:31][CH3:32])([CH3:27])([CH3:26])[CH3:25]>N1C=CC=CC=1.O>[C:24]([O:28][C:29](=[O:34])[C@@H:30]([NH:33][C:8]([C:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH2:31][CH3:32])([CH3:26])([CH3:25])[CH3:27]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 738363-Aminopicolinic acidHCID 53628861tert-Butyl (2S)-2-aminobutanoate--hydrogen chloride (1/1)

Product 1

HCID 67502797HCID 67502797, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 276 mg of 3-aminopyridine-2-carboxylic acid in pyridine (3.0 mL) is added 324 mg of 1,1′-carbonyldiimidazole. The mixture is stirred at room temperature for 2 h. Then 391 mg of (S)-2-amino-butyric acid tert-butyl ester hydrochloride is added and the mixture is stirred for 16 h at room temperature. Then the reaction mixture is diluted with water (1 mL) and concentrated. The residue is diluted with additional 5 mL water and the product is extracted with ethyl acetate (3×5 mL). The combined organic layers are washed with brine, dried (sodium sulfate) and concentrated. The residue is purified by flash chromatography on silica gel to give 218 mg (39%) of (S)-2-[(3-amino-pyridine-2-carbonyl)-amino]-butyric acid tert-butyl ester.

Workup

  1. stirringthe mixture is stirred for 16 h at room temperature
  2. concentrationconcentrated
  3. additionThe residue is diluted with additional 5 mL water
  4. extractionthe product is extracted with ethyl acetate (3×5 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-071887fec533412581cffc80d03b50ea
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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