Sodium ethoxide → HCID 44598988, compound

HRID 656767Notes

Reaction equation

HRID 656767 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-4d97b9754b2c419e88b68cac3968575b
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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