Sodium Hydroxide → HCID 23047407, compound

HRID 2107089Notes

Reaction equation

HRID 2107089 reaction equation
[C:1]1([CH:7]([N:12]([CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21])[C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[C:8]([O:10]C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([CH:7]([N:12]([CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21])[C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23047460HCID 23047460, compound

Product 1

HCID 23047407HCID 23047407, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-phenyl-2-[N-(2,2-dimethoxyethyl)-2-methylpropanamido]acetate (72.3 g) in methanol (800 ml) was treated with a solution of sodium hydroxide (30 g) in water (200 ml). The mixture was stirred for 2.5 hours and then left to stand at room temperature for 18 hours. It was then concentrated to 500 ml and diluted with water (500 ml), washed with diethyl ether (2×200 ml), cooled to below 10° C., and acidified by treatment with hydrochloric acid (4N), maintaining the temperature below 10° C. The precipitated product was extracted with ethyl acetate (3×750 ml) and the combined extracts were washed with brine (300 ml), and evaporated, to give an off-white solid, which was recrystallised from a mixture of ethanol and ethyl acetate and washed with light petroleum, to give 2-phenyl-2-[N-(2,2-dimethoxyethyl)-2-methylpropanamido]acetic acid (67.2 g), in the form of a white solid, m.p. 147°-149° C. [Elemental analysis: C,62.3;H,7.6;N,4.54%; calculated: C,62.1; H,7.4;N,4.53%].

Workup

  1. waitleft
  2. waitto stand at room temperature for 18 hours
  3. concentrationIt was then concentrated to 500 ml
  4. additiondiluted with water (500 ml)
  5. washwashed with diethyl ether (2×200 ml)
  6. temperaturecooled to below 10° C.
  7. temperaturemaintaining the temperature below 10° C
  8. extractionThe precipitated product was extracted with ethyl acetate (3×750 ml)
  9. washthe combined extracts were washed with brine (300 ml)
  10. customevaporated
  11. customto give an off-white solid, which
  12. customwas recrystallised from a mixture of ethanol and ethyl acetate
  13. washwashed with light petroleum

Sources & evidence

ORD record
ord-1e28844b837a42df923f28ca857d606a
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

Loading…