Pyridine → HCID 66976169, compound

HRID 1022712Notes

Reaction equation

HRID 1022712 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([C:17]1[N:18]=[C:19]([CH2:22][C@H:23]2[C@H:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[O:28][CH2:27][CH2:26][N:25]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:24]2)[S:20][CH:21]=1)(=O)[NH2:15].N1C=CC=CC=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1COCC1>[C:14]([C:17]1[N:18]=[C:19]([CH2:22][C@H:23]2[C@H:29]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[O:28][CH2:27][CH2:26][N:25]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:24]2)[S:20][CH:21]=1)#[N:15]

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 516892Sodium BicarbonateHCID 66976736HCID 66976736, compound

Product 1

HCID 66976169HCID 66976169, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic anhydride (0.080 mL, 0.57 mmol) was added to a solution of tert-butyl (6R,7R)-6-[(4-carbamoyl-1,3-thiazol-2-yl)methyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (126 mg, 0.26 mmol) and pyridine (0.084 mL, 1.04 mmol) in THF (4 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight, triethylamine (0.144 mL, 1.04 mmol) and trifluoroacetic anhydride (0.080 mL, 0.57 mmol) were added, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (100 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 15 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36d72147003749428ba6392ff9d6db28
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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