Water → 5-{2-[5-Trifluoromethyl-2-(benzyloxy)phenyl]cyclopent-1-enyl}-3-(2-oxo-pyrrolidin-1-yl)-benzoic acid ethyl ester

HRID 1767218Notes

Reaction equation

HRID 1767218 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[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:7]([NH:34][C:35](=[O:40])[CH2:36][CH2:37][CH2:38]Cl)[CH:6]=1)[CH3:2].[H-].[Na+].O>C1COCC1>[CH2:1]([O:3][C:4](=[O:41])[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:7]([N:34]2[CH2:38][CH2:37][CH2:36][C:35]2=[O:40])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 58887666HCID 58887666, compound

Product 1

HCID 588876585-{2-[5-Trifluoromethyl-2-(benzyloxy)phenyl]cyclopent-1-enyl}-3-(2-oxo-pyrrolidin-1-yl)-benzoic acid ethyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-{2-[5-trifluoromethyl-2-(benzyloxy)phenyl]cyclopent-1-enyl}-3-(4-chloro-butanoylamino) -benzoic acid ethyl ester (140 mg, 0.24 mmol) and NaH (10.5 mg, 0.26 mmol, 60% dispersion in oil) in THF (3 mL), were stirred at room temperature for 4 hrs. The reaction mixture was poured into water and extracted with ethyl acetate (10×3 mL), the combined organic layers were dried over MgSO4 and concentrated. Purification was carried out on a Biotage® using 40% of ethyl acetate in iso-hexane to give the required product as an orange oil (60 mg, 46%). 1H NMR (CDCl3): 1.26(3H,t,J=7.1), 2.01–2.18(4H,m), 2.52(2H,t,J=6.7), 2.88(2H,t,J=7.6), 2.97(2H,t,J=7.4), 3.44(2H,t,J=7.0), 4.26(2H,q,J=7.2), 5.06(2H,s), 6.96(1H,d,J=8.6), 7.18–7.58 (9H, m), 8.09(1H, s).

Workup

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

Sources & evidence

ORD record
ord-b44c422c3d384117b1f0ca6dd6d12776
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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