Sodium Hydroxide → HCID 71656888, compound

HRID 2278174Notes

Reaction equation

HRID 2278174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH:18]([C:23]([O:25]C)=[O:24])[C:19]([F:22])([F:21])[F:20])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.O1CCOCC1.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)[N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH:18]([C:19]([F:22])([F:21])[F:20])[C:23]([OH:25])=[O:24])=[O:16])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 71656887HCID 71656887, compound

Product 1

HCID 71656888HCID 71656888, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of 1,1,1-trifluoro-3-methoxy-3-oxopropan-2-yl 4-(bis(4-chlorophenyl)methyl)piperazine-1-carboxylate (6h) (18 mg, 0.036 mmol) in a 1:1 mixture of 1,4-dioxane:water (1 mL) was added NaOH (360 μL, 0.36 mmol, 1.0 N in water). After stirring the reaction mixture overnight at room temperature, the reaction was quenched by the addition of aqueous 1N HCl (5 mL) and extracted with dichloromethane (3×, 25 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by SiO2 preparative TLC (50% EtOAc/hexanes, 1% HCO2H) to give the title compound as a colorless oil (9.1 mg, 52%): 1H NMR (600 MHz (CDCl3) δ 7.42 (d, J=7.32 Hz, 4H), 7.30 (d, J=8.16 Hz, 4H), 5.35 (s, 1H), 4.53 (bs, 1H), 3.78-3.53 (m, 4H), 2.81-2.54 (m, 4H); HRMS m/z calc'd for [M+H]+ C21H19Cl2F3N2O4: 491.0747. found 491.0735.

Workup

  1. customthe reaction was quenched by the addition of aqueous 1N HCl (5 mL)
  2. extractionextracted with dichloromethane (3×, 25 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by SiO2 preparative TLC (50% EtOAc/hexanes, 1% HCO2H)

Sources & evidence

ORD record
ord-3ae9a914c817454baa6ee6d87624407f
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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