Water → HCID 67503155, compound

HRID 1887199Notes

Reaction equation

HRID 1887199 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@@H:7]([NH:10][C:11]([C:13]1[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22].N12CCCN=C1CCCCC2.O>O1CCCC1>[C:1]([O:5][C:6](=[O:20])[C@@H:7]([N:10]1[C:11](=[O:12])[C:13]2[N:14]=[CH:15][CH:16]=[CH:17][C:18]=2[NH:19][C:21]1=[O:22])[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67502797HCID 67502797, compound

Product 1

HCID 67503155HCID 67503155, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 217 mg of (S)-2-[(3-amino-pyridine-2-carbonyl)-amino]-butyric acid tert-butyl ester in tetrahydrofuran (10 mL) is treated with 259 mg of 1,1′-carbonyldiimidazole and 0.018 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture is stirred at room temperature for 16 h. Then the reaction mixture is added water (1 mL) and the resulting mixture is concentrated and purified by flash chromatography on silica gel to give 130 mg (55%) of (S)-2-(2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-butyric acid tert-butyl ester.

Workup

  1. concentrationthe resulting mixture is concentrated
  2. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e2c1fd4d254b4278b2b97c065f81029a
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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