Water → HCID 19388922, compound

HRID 1757832Notes

Reaction equation

HRID 1757832 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][N:5]([CH2:34][C:35]([O:37]C)=[O:36])[C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]=[C:8]([N+:31]([O-:33])=[O:32])[CH:7]=1.[OH-].[Na+].O>CO.O1CCOCC1>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]=[C:8]([N+:31]([O-:33])=[O:32])[CH:7]=1)[CH2:34][C:35]([OH:37])=[O:36])([OH:39])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19388960HCID 19388960, compound

Product 1

HCID 19388922HCID 19388922, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.44 g (2.6 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-nitro-5-(octadecyloxy) phenyl]glycine methylester and 15 ml of 1N NaOH in 65 ml of methanol, 10 ml of dioxane and 20 mlof water was stirred reflux for 5 hours. The solvents were removed at reduced pressure and the residue was dissolved in 400 ml of hot water. After cooling to room temperature, 6N HCl was added to acidify and the resultant precipitate was filtered. Purification by chromatography on 40 gof silica gel using 20% methanol-chloroform gave 1.1 g (81% yield, mp 131°-134°) of N -(carboxymethyl)-N-[3-nitro-5-(octadecyloxy)phenyl]glycine.

Workup

  1. temperaturereflux for 5 hours
  2. customThe solvents were removed at reduced pressure
  3. dissolutionthe residue was dissolved in 400 ml of hot water
  4. addition6N HCl was added
  5. filtrationthe resultant precipitate was filtered
  6. customPurification by chromatography on 40 gof silica gel using 20% methanol-chloroform

Sources & evidence

ORD record
ord-bd1c9f3753d34cb793756cf251ba3758
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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