Diphosgene → HCID 67502941, compound

HRID 1887195Notes

Reaction equation

HRID 1887195 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].Cl[C:20](OC(Cl)(Cl)Cl)=[O:21]>O1CCCC1.C(=O)(O)[O-].[Na+]>[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:20]1=[O:21])[CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 67501919(R)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester

Product 1

HCID 67502941HCID 67502941, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1.6 g of (R)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester and 0.86 mL of trichloromethyl chloroformate in 25 mL of tetrahydrofuran is stirred at 90° C. for 3 h. The resulting mixture is diluted with saturated sodium bicarbonate solution and the product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography on silica to give 1.75 g (99%) of (R)-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
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica

Sources & evidence

ORD record
ord-1a1fb61c63ec4bb7b34e2fcc42f82af5
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

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