Hydrochloric Acid → HCID 68705549, compound

HRID 1176831Notes

Reaction equation

HRID 1176831 reaction equation
FC1CCCC1.Cl.[CH3:8][O:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][CH:17]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=3)[CH:16]3[CH2:32][CH:33]([OH:35])[CH2:34][CH:15]3[C:14]=2[CH:13]=1>C1COCC1.O>[CH3:8][O:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][CH:17]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:26][CH:27]=3)[CH:16]3[CH2:32][C:33](=[O:35])[CH2:34][CH:15]3[C:14]=2[CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 137022FluorocyclopentaneHCID 68706007HCID 68706007, compound

Product 1

HCID 68705549HCID 68705549, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Preparation 45 (0.012 g) in THF (20 mL) and H2O (1 mL) add HCl solution (2 mL, 3 N in H2O), and stir the mixture overnight. Pour the mixture into satd. NaHCO3 and extract with Et2O (2×50 mL) and EtOAc (2×50 mL). Wash the combined organic extracts with brine, dry over Na2SO4, and concentrate to afford crude Preparation 27 as a light yellow solid. Purify the crude material by MPLC (0% to 25% to 50% EtOAc/hexanes) to afford Example 23 (0.010g, 90%) as a white solid. 1H NMR (CD3OD) δ 7.22 (d, J=8.0 Hz, 2 H), 6.85 (m, 1 H), 6,79 (m, 3 H), 6.64 (m, 1 H), 5.22 (s, 1 H), 3.54 (m, 1 H), 2.67 (m, 1 H), 2.56 (m, 1 H), 2.26 (m, 2 H), 2.13 (m, 2 H), 1.84 (dd, J=3.9, 14.5 Hz, 1 H).

Workup

  1. additionPour the mixture into satd
  2. extractionNaHCO3 and extract with Et2O (2×50 mL) and EtOAc (2×50 mL)
  3. washWash the combined organic extracts with brine
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate
  6. customto afford crude
  7. customPurify the crude material by MPLC (0% to 25% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-49446a8dc2d74d4bb00c73294a46545b
Source dataset
uspto-grants-2010_11
Patent number
US07842822B2

Reaction notes

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