Water → HCID 60128074, compound

HRID 1454024Notes

Reaction equation

HRID 1454024 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([C@H:12]([CH3:16])[C:13]([OH:15])=[O:14])[CH2:7][CH2:6]2.[C:17](=O)(O)[O-].[Na+].IC.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([C@H:12]([CH3:16])[C:13]([O:15][CH3:17])=[O:14])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 516892Sodium BicarbonateHCID 60128073HCID 60128073, compound

Product 1

HCID 60128074HCID 60128074, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of (2S)-2-[(1S)-5-methoxy-2,3-dihydro-1H-inden-1-yl]propanoic acid (Example 10) (6.45 g, 0.029 mol), sodium bicarbonate (7.380 g, 0.088 mol), and iodomethane (5.5 mL, 0.088 mol) in DMF (60 mL) was stirred at rt for a period of 17 h. The completion of the reaction was achieved by addition of an additional amount of iodomethane (0.93 mL, 0.015 mol) and stirring for another 3 h at rt. The reaction mixture was poured into water (200 mL) and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with NaOH (1 N aqueous solution), water and brine, dried (Na2SO4), filtered, and concentrated to dryness under vacuum to give 5.70 g (84%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 6.96 (d, 1H), 6.77 (d, 1H), 6.67 (dd, 1H), 3.70 (s, 3H), 3.63 (s, 3H), 3.38 (q, 1H), 2.78 (m, 3H), 2.08 (m, 1H), 1.78 (m, 1H); LC-MS RT=3.10 min; (M+H)+ 234.9.

Workup

  1. stirringstirring for another 3 h at rt
  2. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with NaOH (1 N aqueous solution), water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-d78e98d6e4a34afc8c919f5c7e5f3ba7
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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