Methyl iodide → HCID 131736590, compound

HRID 1479839Notes

Reaction equation

HRID 1479839 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH:17]([OH:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:20]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[CH3:20][N:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])[C@@H:12]([CH:17]([OH:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 131736591HCID 131736591, compound

Product 1

HCID 131736590HCID 131736590, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 9A (5.5 g, 19 mmol) dissolved in DMF (15 ml) was added with K2CO3 (1.1 equiv., 2.75 g) and methyl iodide (1.1 equiv., 1.94 ml) and the reaction was stirred at rt overnight. The reaction was diluted with ethyl acetate and washed several times with water and finally with Brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from ethyl ether and petroleum ether afforded 5 g of 10A as a semisolid. Yield=86%. 1HNMR (DMSO, 200 MHz) δ 1.10 (3H, d, J=6.2 Hz), 2.94 (3H, s), 3.46 (3H, s), 4.22 (1H, q, J=6.4 Hz), 4.39 (1H, d, J=5.2 Hz), 5.16 (1H, d, J=3.2 Hz), 7.40 (2H, m), 7.82 (2H, m)

Workup

  1. washwashed several times with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe purification of the crude residue
  5. customby crystallization from ethyl ether and petroleum ether

Sources & evidence

ORD record
ord-c23f02dea5db4654ae8a0061d6c4a9be
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

Loading…