Water → HCID 58887655, compound

HRID 1767217Notes

Reaction equation

HRID 1767217 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:7]([NH2:34])[CH:6]=1)[CH3:2].N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44].O>CN(C1C=CN=CC=1)C.ClCCl>[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:7]([NH:34][S:43]([CH3:42])(=[O:45])=[O:44])[CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 588876235-{2-[5-Trifluoromethyl-2-benzyloxyphenyl]cyclopent-1-enyl}-3-aminobenzoic acid ethyl ester

Product 1

HCID 58887655HCID 58887655, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-{2-[5-trifluoromethyl-2-(benzyloxy)phenyl]cyclopent-1-enyl)-3-aminobenzoic acid ethyl ester (60 mg, 0.12 mmol), pyridine (11 μL, 0.137 mmol), methane sulphonyl chloride (11 μL, 0.137 mmol), and a catalytic amount of DMAP in 2 mL of dichloromethane were stirred at room temperature for 2 hrs. The reaction mixture was poured into water and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. Purification was carried out on a SPE using iso-hexane containing a gradient of ethyl acetate (5–30%) to give the required product as yellow oil (55 mg, 78%). 1H NMR (CDCl3):1.32 (3H,t,J=7.1), 2.06–2.13 (2H,m), 2.60(3H,s), 2.88 (2H,t,J=7.4), 2.92–296(2H,m), 4.31 (2H,q,J=7.1), 5.11 (2H,s), 6.42 (1H,s), 7.04 (1H,d,J=8.6), 7.11 (1H,s), 7.23–7.30 (5H,m), 7.33(1H,d), 7.54 (1H,s), 7.66 (1H,s). LC/MS[MH−]=558 Rt=4.11.

Workup

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

Sources & evidence

ORD record
ord-944830cbdf5e4a82b4168a35c54b4b72
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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