Water → HCID 69508212, compound

HRID 1767239Notes

Reaction equation

HRID 1767239 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:8]=C(N)[CH:6]=1)[CH3:2].[C:36](=O)([O-])[O-].[K+].[K+].[CH2:42](I)[CH3:43].O.C[N:47]([CH:49]=O)[CH3:48]>>[CH2:1]([O:3][C:4](=[O:35])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=[CH:18][C:17]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:8]=[C:48]([N:47]([CH2:42][CH3:43])[CH2:49][CH3:36])[CH:6]=1)[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 588876235-{2-[5-Trifluoromethyl-2-benzyloxyphenyl]cyclopent-1-enyl}-3-aminobenzoic acid ethyl ester

Product 1

HCID 69508212HCID 69508212, compound

Procedure

5-{2-[5-trifluoromethyl-2-benzyloxyphenyl]cyclopent-1-enyl}-3-aminobenzoic acid ethyl ester (90 mg, 0.18 mmol), potassium carbonate (51 mg, 0.37 mmol), ethyliodide (0.037 mL, 0.47 mmol), in 3 mL of DMF were stirred at 40° C. for 16 hrs, another 0.037 mL of ethyl iodide were added and the reaction mixture was stirred for another 4 hrs. The mixture was then poured into water and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), and concentrated. Purification was carried out on SPE using a gradient of iso-hexane/ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification

Sources & evidence

ORD record
ord-dd5065050bfc4987b27955ee3fed5e4b
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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