Sodium ethoxide → HCID 67064546, compound

HRID 601215Notes

Reaction equation

HRID 601215 reaction equation
[CH:1](=[N:8][N:9]([C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([O:25]C)=O)[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+]>C(O)C>[OH:25][C:23]1[C:19]2[S:20][CH:21]=[CH:22][C:18]=2[N:9]([N:8]=[CH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10](=[O:17])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 67063420HCID 67063420, compound

Product 1

HCID 67064546HCID 67064546, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of the product of Example 268B (37.8 g, 0.101 mol) in ethanol (0.5 L) under nitrogen was reacted with sodium ethoxide in ethanol (21% by weight, 32.8 g, 0.104 mol) at room temperature. The mixture was slowly warmed to 50° C. and stirred for 1 hour at 40-50° C., cooled to 25° C., partitioned between ethyl acetate and water, and acidified to pH 4 with 1 M hydrochloric acid. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (12.0 g, 35%). 1H NMR (300 MHz, CDCl3) δ ppm 1.47 (t, J=7.17 Hz, 3 H) 4.52 (q, J=7.23 Hz, 2 H) 7.33 (d, J=5.15 Hz, 1 H) 7.50 (m, 3 H) 7.75 (d, J=5.52 Hz, 1 H) 7.88 (dd, J=7.72, 1.84 Hz, 2 H) 9.44 (s, 1 H) 14.16 (s, 1 H).

Workup

  1. temperaturecooled to 25° C.
  2. custompartitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f4e6e6b8f1c423eb2947224a273acf7
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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