Pyridine → HCID 23387338, compound

HRID 1170567Notes

Reaction equation

HRID 1170567 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:31][C:32]([CH3:38])([CH2:36]O)[C:33]([OH:35])=[O:34].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:31][C:32]([CH3:38])([CH2:36][O:14][C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[C:33]([OH:35])=[O:34]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 83693Boc-L-Valine

Product 1

HCID 23387338HCID 23387338, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-Boc-L-valine (10.8 g, 50 mmole), 4-dimethylaminopyridine (610 mg, 5 mmole) and DCC (6.18 g, 30 mmole) were dissolved in methylene chloride (100 ml). After stirring for 2 hour the mixture was filtered. To the filtrate were added 2,2-dimethyl-3-hydroxy-propionic acid (3.54 g, 30 mmole) and pyridine (10 ml). After 18 hr, the reaction mixture was filtered, and the filtrate was poured into sodium hydrogen carbonate aqueous solution, the organic phase was then washed with citric acid aqueous solution and water successively. After evaporation the product was isolated with silica gel column chromatography to yield 4.4 g. This compound can be activated and esterified directly to a drug or further modified as described below.

Workup

  1. filtrationwas filtered
  2. waitAfter 18 hr
  3. filtrationthe reaction mixture was filtered
  4. additionthe filtrate was poured into sodium hydrogen carbonate aqueous solution
  5. washthe organic phase was then washed with citric acid aqueous solution and water successively
  6. customAfter evaporation the product
  7. customwas isolated with silica gel column chromatography
  8. customto yield 4.4 g

Sources & evidence

ORD record
ord-bc7393fdaec145c08da1a8cf082eb199
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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