Sodium Hydroxide → HCID 59225742, compound

HRID 387502Notes

Reaction equation

HRID 387502 reaction equation
[CH:1]1([C:7]2[C:8]([C:24]([O:26]CC)=[O:25])=[C:9]([NH:12][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)=[O:14])[S:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([C:7]2[C:8]([C:24]([OH:26])=[O:25])=[C:9]([NH:12][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)=[O:14])[S:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59225737HCID 59225737, compound

Product 1

HCID 59225742HCID 59225742, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 51 (0.2 mmol) in EtOH (2 ml) at room was added 1.0 N NaOH (aq.) (0.2 ml). The mixture was stirred at 100° C. for 17 hrs. The solvent was removed under vacuum. The residue was suspended in 1.0 N HCl (aq.) (2 ml) and extracted with ethyl acetate (3×5 ml). The combined organic layers were dried over anhydrous sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under vacuum to give the crude product which was purified using preparative HPLC to give 52 (40.9 mg). 1H NMR (DMSO-d6) δ 1.27 (m, 6H), 1.73 (m, 2H), 1.90 (m, 2H), 3.09 (m, 1H) 3.57 (s, 1H), 6.74 (s, 1H). 7.20 (m, 1H), 7.53 (m, 2H), 12.34 (s, 1H) ppm.

Workup

  1. customThe solvent was removed under vacuum
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationThe filtrate was concentrated under vacuum
  6. customto give the crude product which
  7. customwas purified

Sources & evidence

ORD record
ord-2d487f473f494e6b8a2cd7a5d2eaac64
Source dataset
uspto-grants-2013_02
Patent number
US08372991B2

Reaction notes

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