Sodium Hydroxide → N-(carboxymethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy]phenyl]ethyl]glycine

HRID 488335Notes

Reaction equation

HRID 488335 reaction equation
C([O:3][C:4](=[O:43])[CH2:5][N:6]([CH2:37][C:38]([O:40]CC)=[O:39])[C:7](=[O:36])[C:8](=[O:35])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+]>CO>[C:38]([CH2:37][N:6]([C:7](=[O:36])[C:8](=[O:35])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:11][CH:10]=1)[CH2:5][C:4]([OH:43])=[O:3])([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091810N-(2-ethoxy-2-oxoethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy] phenyl]ethyl]glycine ethyl ester

Product 1

HCID 19091794N-(carboxymethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy]phenyl]ethyl]glycineYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.3 g (2.17 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy]phenyl]ethyl]glycine ethyl ester and 1.8 ml (10.8 mmol) of 6N NaOH in 125 ml of methanol was stirred at reflux for 3.5 hours. The reaction mixture was cooled in an ice bath and the precipitated sodium salt was filtered. The sodium salt was suspended in water, acidified with 6N HCl and extracted with ethyl acetate. The dried extract was concentrated to a solid which was triturated with hexane and filtered to give 1.04 g (88% yield, mp 130°-132°) of N-(carboxymethyl)-N-[1,2-dioxo-2-[4-[(12-phenoxydodecyl)oxy]phenyl]ethyl]glycine.

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. filtrationthe precipitated sodium salt was filtered
  4. extractionextracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas triturated with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-2ec83afb10cf43ac986cf55dc19a0e76
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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