Sodium Hydroxide → HCID 67970440, compound

HRID 889537Notes

Reaction equation

HRID 889537 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:20]([F:22])[F:21])=[C:14]([CH:19]=1)[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH:20]([F:21])[F:22])=[C:14]([CH:19]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67970381HCID 67970381, compound

Product 1

HCID 67970440HCID 67970440, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Treat a solution of methyl 5-(tert-butoxycarbonylaminomethyl)-2-(difluoromethyl)benzoate (1.43 g, 4.54 mmol, 1.0 equiv) in 1,4-dioxane (20 mL) with sodium hydroxide (5 N aqueous, 1.81 mL, 9.07 mmol, 2.0 equiv), and stir the mixture at room temperature overnight. Concentrate under reduced pressure, and adjust the pH to 4 with aqueous HCl. Extract with EtOAc (2×40 mL), and wash the combined organic extracts with saturated aqueous NaCl, separate, and dry the organic phase over Na2SO4, filter, and concentrate under reduced pressure to give the title compound (1.21 g, 88%). MS (m/z) 319 (M+18).

Workup

  1. concentrationConcentrate under reduced pressure
  2. extractionExtract with EtOAc (2×40 mL)
  3. washwash the combined organic extracts with saturated aqueous NaCl
  4. customseparate
  5. dry with materialdry the organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-bc2c6d706a4a4b61bce844e9dab60b1c
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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