Sodium Hydroxide → HCID 59385441, compound

HRID 2356850Notes

Reaction equation

HRID 2356850 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][CH:13]([O:18][CH3:19])[C:14]([O:16]C)=[O:15])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][CH:13]([O:18][CH3:19])[C:14]([OH:16])=[O:15])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59385469HCID 59385469, compound

Product 1

HCID 59385441HCID 59385441, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-[(3,5-difluorophenyl)acetylamino]-2-methoxyacetate 2A (0.4 g) was dissolved in 10 mL of dioxane and treated with 2.8 mL of a 1.0 N aqueous sodium hydroxide solution. After 1.5 h most of the solvent was removed by evaporation at reduced pressure. The mixture was acidified with an aqueous solution of sodium bisulfate and washed with two successive portions of ether. The combined organic extracts were washed with brine and then dried with magnesium sulfate. The solution was filtered and the solvent was evaporated at reduced pressure to yield 2-[(3,5-Difluorophenyl)acetylamino]-2-methoxyacetic acid 3 as 0.35 g of a white powder. 1H-NMR (DMSO-d6): δ 9.06 (d, J=8.7 Hz, 1H), 7.15-6.85 (m, 3H), 5.23 (d, J=8.7 Hz, 1H), 3.57 (s, 3H), 3.21 (s, 2H).

Workup

  1. customAfter 1.5 h most of the solvent was removed by evaporation at reduced pressure
  2. washwashed with two successive portions of ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-4e48e9e06dcb45b792ad4c83a3215fd3
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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