Sodium Hydroxide → HCID 19389134, compound

HRID 1757803Notes

Reaction equation

HRID 1757803 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][N:5]([CH2:32][C:33]([O:35]C)=[O:34])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:31])[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:7]=1.[OH-].[Na+]>O1CCOCC1.CO>[C:3]([CH2:4][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:31])[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:7]=1)[CH2:32][C:33]([OH:35])=[O:34])([OH:37])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19018993HCID 19018993, compound

Product 1

HCID 19389134HCID 19389134, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.8 g N-(2-methoxy-2-oxoethyl)-N-[3-[(1-oxooctadecyl)amino]phenyl]glycine methylester and 2.4 ml of 6N NaOH in 30 ml of dioxane and 30 ml of methanol was heated to dissolve the solid and left at room temperature for 18 hours. The solid which precipitated was filtered, treated with 1N HCl and filtered again. Recrystallization from methanol-THF-water gave 1.35 g (79%yield, mp 133°-140°) of N-(carboxymethyl)-N-[3-[(1-oxooctadecyl)amino]phenyl]glycine.

Workup

  1. temperaturewas heated
  2. dissolutionto dissolve the solid
  3. customThe solid which precipitated
  4. filtrationwas filtered
  5. additiontreated with 1N HCl
  6. filtrationfiltered again
  7. customRecrystallization from methanol-THF-water

Sources & evidence

ORD record
ord-9d41753ca4d4419f8c0b7779c9c65b8a
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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