Sodium ethoxide → HCID 44598988, compound

HRID 888514Notes

Reaction equation

HRID 888514 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][CH2:25][CH2:26]Cl)=[O:23])=[CH:17][C:16]=2[CH2:28][S:29][CH2:30][C:31]([F:34])([F:33])[F:32])[CH:7]=1)C.[O-]CC.[Na+]>CCO>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:3])=[O:35])=[CH:7][C:8]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][O:24][C:22]2=[O:23])=[CH:17][C:16]=1[CH2:28][S:29][CH2:30][C:31]([F:34])([F:32])[F:33]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58372793HCID 58372793, compound

Product 1

HCID 44598988HCID 44598988, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To {3-[4-(2-chloro-ethoxycarbonylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester (0.100 g, 0.19 mmol) in EtOH (5 mL) was added sodium ethoxide (21 wt % in EtOH; 4.61 mL, 0.37 mmol), and the reaction was stirred at 65° C. overnight. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9b5d46ca82b4421abee3ddcf5945fe41
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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