Sodium Hydroxide → HCID 86620046, compound

HRID 1993976Notes

Reaction equation

HRID 1993976 reaction equation
[N+](C1C=CC(C([O:10][CH2:11][C@@H:12]2[C@@H:17]([CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:16]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C@@H:15]([O:34][C@@H:35]([C:37]3[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=3)[CH3:36])[O:14][CH2:13]2)=O)=CC=1)([O-])=O.[OH-].[Na+]>CO.C(O)C.CCOC(C)=O>[CH2:20]([O:19][CH2:18][C@H:17]1[C@H:16]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[C@@H:15]([O:34][C@@H:35]([C:37]2[CH:42]=[C:41]([C:43]([F:46])([F:44])[F:45])[CH:40]=[C:39]([C:47]([F:50])([F:48])[F:49])[CH:38]=2)[CH3:36])[O:14][CH2:13][C@@H:12]1[CH2:11][OH:10])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86620044HCID 86620044, compound

Product 1

HCID 86620046HCID 86620046, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
45 °C

Procedure

The intermediate from example 1 step H (4.57 g, 6.22 mmol) was dissolved in a 1:1 mixture of methanol/ethanol (60 mL) followed by the addition of 5 N NaOH (12.0 mL). The vessel was heated to 45° C. for 1 hr. The reaction mixture was cooled to ambient temperature and diluted with 400 mL EtOAc. The EtOAc solution was washed twice with 2 N NaOH, dried over Na2SO4, filtered through a fritted funnel and concentrated in vacuo. The crude residue was purified on silica gel and eluted a combination of EtOAc/hexanes (1-30% EtOAc/hexanes linear gradient). This provided the title compound. 1H-NMR (CDCl3): δ 1.38 (d, 3H, J=6.5 Hz), 1,90-2.22 (m, 2H), 2.34-2.42 (m, 1H), 2.72 (dd, 1H, J=8.5, 10.5 Hz), 3.12-3.18 (m, 1H), 3.24-3.31 (m, 1H), 3.46-3.56 (m, 2H), 3.55-3.62 (m, 1H), 3.65-3.74 (m, 1H), 4.09 (dd, 1H, J=4.0, 11.5 Hz), 4.21 (d, 1H, J=8.5 Hz), 4.31 (s, 21H), 4.96 (q, 1H, J=6.5 Hz), 6.90-7.02 (m, 4H), 7.14-7.22 (m, 4H), 7.25-7.34 (m, 3H), 7.69 (s, 1H) ppm.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe EtOAc solution was washed twice with 2 N NaOH
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through a fritted funnel
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on silica gel
  7. washeluted a combination of EtOAc/hexanes (1-30% EtOAc/hexanes linear gradient)

Sources & evidence

ORD record
ord-af978beaac294191a09f19da61f67d68
Source dataset
uspto-grants-2010_01
Patent number
US07652058B2

Reaction notes

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