Hydrochloric Acid → HCID 58934741, compound

HRID 854871Notes

Reaction equation

HRID 854871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:19])[C:11]=1[O:12][CH2:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[O:8][CH:7]([C:20]([F:23])([F:22])[F:21])[C:6]([C:24]([O:26]C)=[O:25])=[CH:5]2.[OH-].[Na+].Cl>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:19])[C:11]=1[O:12][CH2:13][CH:14]([CH2:15][CH3:16])[CH2:17][CH3:18])[O:8][CH:7]([C:20]([F:23])([F:21])[F:22])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69517977HCID 69517977, compound

Product 1

HCID 58934741HCID 58934741, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 3 (0.55 g, 1.35 mmole) was dissolved in 3.5 mL methanol and 3.5 mL THF. Sodium hydroxide (2.5 N) (1.6 mL, 4 mmole) was added to above solution and stirred at room temperature overnight. The reaction mixture was acidified with 1.5 N HCl. The compound was extracted with EtOAc. The organic layer was washed with water and dried over anhydrous MgSO4. The filtrate was evaporated and dried in vacuo, after recrystalization with EtOH and water to afford a yellow solid (0.31 g, 59%): ESHRMS m/z391.0884 (M−H, C18H19O4F3Cl, Calc'd 391.0918). 1H NMR (acetone-d6/400 MHz) 7.84 (s, 1H), 7.45 (s, 1H), 5.88 (q, 1H, J=7.0 Hz), 3.92 (m, 2H), 2.17 (s, 3H), 1.71 (m, 1H), 1.61 (m, 2H), 1.53 (m, 2H), 0.971 (t, 6H, J=7.2 Hz).

Workup

  1. extractionThe compound was extracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe filtrate was evaporated
  5. customdried in vacuo
  6. customafter recrystalization with EtOH and water

Sources & evidence

ORD record
ord-7a5b68027bc345babaeb3e8f7015c1e3
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…