Pyridine → HCID 21112786, compound

HRID 1767114Notes

Reaction equation

HRID 1767114 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:18]1C=CC=CC=1.C(OC(OCCCC)=O)(OCCCC)=O.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[NH2:18][C:15]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 14200314Dibutyl dicarbonate

Product 1

HCID 21112786HCID 21112786, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of the commercially available 4-[(tert-butoxycarbonyl)amino]tetrahydro-2H-pyran-4-carboxylic acid in dioxane, pyridine (0.6 eq.), di-butyl dicarbonate (1.3 eq) and ammonium bicarbonate (1.26 eq) were added and the mixture was stirred at room temperature for 20 hours. Dioxane was concentrated and the residue dissolved in ethyl acetate and washed with HCl 1N, saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and evaporated in vacuo to obtain the solid compound (C-25).

Workup

  1. concentrationDioxane was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with HCl 1N, saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto obtain the solid compound (C-25)

Sources & evidence

ORD record
ord-8909113bde87498ea59ac7eed76972c5
Source dataset
uspto-grants-2007_06
Patent number
US07232819B2

Reaction notes

Loading…