Sodium ethoxide → HCID 44599644, compound

HRID 888534Notes

Reaction equation

HRID 888534 reaction equation
[O-]CC.[Na+].C([O:7][C:8](=[O:39])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH2:29][CH2:30]Cl)=[O:27])=[CH:21][C:20]=2[CH2:32][S:33][CH2:34][C:35]([F:38])([F:37])[F:36])[CH:11]=1)C>CCO>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C:8]([OH:7])=[O:39])=[CH:11][C:12]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][C:26]2=[O:27])=[CH:21][C:20]=1[CH2:32][S:33][CH2:34][C:35]([F:37])([F:36])[F:38]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 58372726HCID 58372726, compound

Product 1

HCID 44599644HCID 44599644, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Sodium ethoxide (20% wt/v; 2.27 mL, 0.187 mmol) was added to a solution of {3-[4-[3-(2-chloro-ethyl)-ureido]-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester (0.050 g, 0.094 mmol) in EtOH (5 mL). The reaction was stirred at 65° C. overnight, and then partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by preparative HPLC to give Compound 57.

Workup

  1. custompartitioned 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-c994f6beb8324bdf87f74ce76b71344d
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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