1,1'-Carbonyldiimidazole → HCID 67502136, compound

HRID 1887192Notes

Reaction equation

HRID 1887192 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@@H:5]([NH:8][C:9]([C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:10])[CH2:6][CH3:7].[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20].N12CCCN=C1CCCCC2>O1CCCC1.O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@@H:5]([N:8]1[C:9](=[O:10])[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:16]=2[NH:17][C:19]1=[O:20])[CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67503115(S)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester

Product 1

HCID 67502136HCID 67502136, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 250 mg of (S)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester in tetrahydrofuran (10 mL) is added 403 mg of 1,1′-carbonyldiimidazole and 0.04 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene at room temperature and the mixture is stirred at room temperature for 60 h. The reaction mixture is diluted with 50 mL of water and the product is extracted with ethyl acetate (50 mL×3). The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash chromatography on silica gel to give 250 mg (91%) of (S)-3-(2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-pentanoic acid methyl ester.

Workup

  1. extractionthe product is extracted with ethyl acetate (50 mL×3)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d93c6c1e791f4e41a0e2b50ad9644048
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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