Sodium Hydroxide → HCID 66670136, compound

HRID 1014923Notes

Reaction equation

HRID 1014923 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=2)[N:17](C(=O)C)[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([F:24])=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66809318HCID 66809318, compound

Product 1

HCID 66670136HCID 66670136, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing 65 (2.2 g, 0.006 mol) in MeOH (15 mL) was added 1M NaOH (6 mL, 0.006 mol) at 0° C. After 30 min, TLC analysis revealed complete consumption of 65 [EtOAc/hexanes 1:1, Rf(65) 0.6; Rf(66)=0.5]. The solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic phase was washed with 1M HCl, water, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 2.11 g (quant.) of crude 66 which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ9.0 (s, 1H, major rotamer), 8.85 (s, minor rotamer), 7.62-7.5 (m, 1H), 7.1-6.72 (m, 3H), 3.8-2.7 (m, 5H), 2.15-1.3 (m, 3H), 1.55 (s, 9H), 0.85 (d, J=7 Hz, 3H) ppm.

Workup

  1. customconsumption of 65 [EtOAc/hexanes 1:1, Rf(65) 0.6; Rf(66)=0.5]
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic phase was washed with 1M HCl, water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford 2.11 g (quant.) of crude 66 which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-df27a183213d432daaa0672b664fd1d3
Source dataset
uspto-grants-2011_07
Patent number
US07985735B2

Reaction notes

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