Methyl iodide → HCID 86706196, compound

HRID 529456Notes

Reaction equation

HRID 529456 reaction equation
IC.[C:3]([O-])([O-])=O.[K+].[K+].[O:9]=[C:10]1[C@@H:16]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14][S:13][C@H:12]2[CH2:24][CH2:25][CH2:26][C@@H:27]([C:28]([O:30][CH3:31])=[O:29])[N:11]12>CN(C=O)C>[O:9]=[C:10]1[C@@H:16]([N:17]([CH3:3])[C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])[CH2:15][CH2:14][S:13][C@H:12]2[CH2:24][CH2:25][CH2:26][C@@H:27]([C:28]([O:30][CH3:31])=[O:29])[N:11]12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86706195HCID 86706195, compound

Product 1

HCID 86706196HCID 86706196, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (77 mg, 0.54 mmol) and K2CO3 (150 mg, 1.08 mmol) were added to a solution of (4S,7S,10aS)-methyl 5-oxo-4-(2,2,2-trifluoroacetamido)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (64 mg, 0.18 mmol) in DMF (1 mL). The reaction mixture was stirred at rt overnight. The reaction mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated NaHCO3 and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give (4S,7S,10aS)-methyl 5-oxo-4-(2,2,2-trifluoro-N-methylacetamido)octahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (47.6 mg, 0.129 mmol, 72% yield) of a yellow oil. Anal. Calcd. for C14H19F3N2O4S m/z 368.3. found: 391.1 (M+Na)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe organic phase was isolated
  3. washwashed with saturated NaHCO3 and saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-811521d5da6c46fa96ccf9a59d2cec5c
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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