Potassium Carbonate → HCID 59915831, compound

HRID 529457Notes

Reaction equation

HRID 529457 reaction equation
C([O-])([O-])=O.[K+].[K+].[O:7]=[C:8]1[C@@H:14]([N:15](C)[C:16](=O)C(F)(F)F)[CH2:13][CH2:12][S:11][C@H:10]2[CH2:23][CH2:24][CH2:25][C@@H:26]([C:27]([O:29][CH3:30])=[O:28])[N:9]12>O.CO>[CH3:16][NH:15][C@H:14]1[CH2:13][CH2:12][S:11][C@H:10]2[CH2:23][CH2:24][CH2:25][C@@H:26]([C:27]([O:29][CH3:30])=[O:28])[N:9]2[C:8]1=[O:7]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86706196HCID 86706196, compound

Product 1

HCID 59915831HCID 59915831, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of K2CO3 (18.8 mg, 0.136 mmol) in water (0.16 mL) was added to a solution of (4S,7S,10aS)-methyl 5-oxo-4-(2,2,2-trifluoro-N-methylacetamido)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (45.6 mg, 0.124 mmol) in MeOH (0.4 mL). The reaction mixture was stirred at rt for 2 hr. After a total of 3 hr, a stream of nitrogen gas was used to partially evaporate the MeOH. The residue was then partitioned between CHCl3 and saturated aqueous NaCl. The aqueous layer was isolated and extracted once again with CHCl3. All organic phases were combined, dried over MgSO4 and concentrated to give (4S,7S,10aS)-methyl 4-(methylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (34 mg, 0.12 mmol, 100% yield) of a yellow oil. Anal. Calcd. for C12H20N2O3S m/z 272.3. found: 273.2 (M+H)+.

Workup

  1. customAfter a total of 3 hr
  2. customto partially evaporate the MeOH
  3. customThe residue was then partitioned between CHCl3 and saturated aqueous NaCl
  4. customThe aqueous layer was isolated
  5. extractionextracted once again with CHCl3
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f966e61a4d564714a4d4a961e48eec9d
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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