Methyl iodide → HCID 58499665, compound

HRID 910784Notes

Reaction equation

HRID 910784 reaction equation
[CH:1](NC(C)C)(C)C.IC.[C:10]([O:14][C:15](=[O:27])[NH:16][C@@H:17]([C:19]1[N:23]([CH2:24][CH3:25])[C:22]([SH:26])=[N:21][N:20]=1)[CH3:18])([CH3:13])([CH3:12])[CH3:11]>O1CCCC1>[C:10]([O:14][C:15](=[O:27])[NH:16][C@@H:17]([C:19]1[N:23]([CH2:24][CH3:25])[C:22]([S:26][CH3:1])=[N:21][N:20]=1)[CH3:18])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 178462987HCID 178462987, compound

Product 1

HCID 58499665HCID 58499665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylamine (17.4 ml) and iodomethane (7.7 ml) were added to a tetrahydrofuran (200 ml) solution of the [(R)-1-(4-ethyl-5-mercapto-4H-[1,2,4]triazol-3-yl)ethyl]-carbamic acid t-butyl ester (28.12 g) obtained in Example 8-(3). The mixture was stirred for 1 hour at room temperature, and then precipitated crystals were filtered. The filtrate was concentrated, and the resulting crude crystals were washed with a hexane-ethyl acetate solvent mixture (3:1, 200 ml), followed by drying, to obtain [(R)-1-(4-ethyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)ethyl]-carbamic acid t-butyl ester as a white powder (29.5 g).

Workup

  1. customprecipitated crystals
  2. filtrationwere filtered
  3. concentrationThe filtrate was concentrated
  4. washthe resulting crude crystals were washed with a hexane-ethyl acetate solvent mixture (3:1, 200 ml)
  5. customby drying

Sources & evidence

ORD record
ord-530174cec36a42cc911e73e4a8b146b0
Source dataset
uspto-grants-2011_09
Patent number
US08022225B2

Reaction notes

Loading…