Pyridine → HCID 56602548, compound

HRID 1809441Notes

Reaction equation

HRID 1809441 reaction equation
[CH3:1][C:2]([C:7]1[CH:11]=[C:10]([NH:12][C:13](=[O:26])[C:14]([CH3:25])([S:16]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH3:15])[O:9][N:8]=1)([CH3:6])[C:3](O)=[O:4].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+].[N:47]1C=CC=CC=1>C(OCC)(=O)C.O1CCOCC1.CN(C=O)C>[CH3:15][C:14]([S:16]([CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)(=[O:17])=[O:18])([CH3:25])[C:13]([NH:12][C:10]1[O:9][N:8]=[C:7]([C:2]([CH3:6])([CH3:1])[C:3]([NH2:47])=[O:4])[CH:11]=1)=[O:26]

Participants

8

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 56602957HCID 56602957, compound

Product 1

HCID 56602548HCID 56602548, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methyl-2-{5-[2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionylamino]-isoxazol-3-yl}-propionic acid (35 mg, 0.09 mmol), di-tert-butyl dicarbonate (26 mg, 0.12 mmol), and ammonium bicarbonate (14 mg, 0.18 mmol) in the mixture of DMF (0.035 mL) and 1,4-dioxane (0.5 mL) is added pyridine (0.022 mL, 0.27 mmol). The reaction mixture is stirred at room temperature for 1.5 h. After this time, the reaction mixture is diluted with ethyl acetate and washed with 1N aqueous hydrochloric acid solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the residue by preparative HPLC provides 3.0 mg of the title compound. Yield: 9%; m/z 388 [M+H].

Workup

  1. washwashed with 1N aqueous hydrochloric acid solution and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by preparative HPLC

Sources & evidence

ORD record
ord-889c09259400452faf6a62e063e0a719
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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