Pyridine → HCID 21112786, compound

HRID 2373512Notes

Reaction equation

HRID 2373512 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-716bd1e26287468d96a36d452fabb36f
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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