Methyl iodide → HCID 178500945, compound

HRID 1623570Notes

Reaction equation

HRID 1623570 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=1[F:21])=[S:9])=[O:6].[CH3:23]C([O-])(C)C.[Na+].IC.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5](/[N:7]=[C:8](/[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:20])[F:19])[C:12]=1[F:21])\[S:9][CH3:23])=[O:6]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxide2×HCID 59627500HCID 59627500, compound

Product 1

HCID 178500945HCID 178500945, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

An ice-cooled solution of intermediate D19 (17.1 g) in THF (450 ml) was stirred under an atmosphere of N2. NaOtBu (1 eq) was added and after 30 minutes a solution of iodomethane (3.15 ml) in THF was added dropwise. After another 30 minutes an additional NaOtBu (1 eq) was added and the contents stirred at ˜0° C. When the reaction was completed after 45 minutes, a saturated solution of NH4Cl was added and the reaction was diluted with EtOAc. The phases were separated and the aqueous phase extracted with EtOAc (×2). The combined organic extracts were washed with brine, then dried (Na2SO4). Filtration and concentration under reduced pressure gave the crude material as an amber oil. Yield: 17.2 g of intermediate D20 (59%).

Workup

  1. additionwas added dropwise
  2. stirringthe contents stirred at ˜0° C
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with EtOAc (×2)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-b076874ba47d422dbd4e1dab50d703bc
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

Loading…