Sodium Hydroxide → HCID 19091777, compound

HRID 488306Notes

Reaction equation

HRID 488306 reaction equation
C([O:3][C:4](=[O:48])[CH2:5][N:6]([CH2:42][C:43]([O:45]CC)=[O:44])[C:7](=[O:41])[C:8]1[CH:13]=[C:12]([O: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][CH2:30][CH2:31][CH3:32])[CH:11]=[CH:10][C:9]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)C.[OH-].[Na+]>CO>[C:43]([CH2:42][N:6]([C:7](=[O:41])[C:8]1[CH:13]=[C:12]([O: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][CH2:30][CH2:31][CH3:32])[CH:11]=[CH:10][C:9]=1[O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH2:5][C:4]([OH:48])=[O:3])([OH:45])=[O:44]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091761HCID 19091761, compound

Product 1

HCID 19091777HCID 19091777, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.6 g (9.9 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[5-(octadecyloxy)-2-(phenylmethoxy)benzoyl]glycine ethyl ester and 25 ml (50 mmol) of 2N NaOH in 300 ml of methanol was stirred at reflux for 2 hours. The solvent was removed at reduced pressure, the residue was acidified and the product was extracted with ethyl acetate. The dried extract was concentrated to an oil which was treated with water and cooled in the refrigerator. The resultant solid was filtered, triturated with ether-hexane and filtered again to give 5.8 g (96% yield, mp 81°-83°) of N-(carboxymethyl)-N-[5-(octadecyloxy)-2-(phenylmethoxy)benzoyl]glycine.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed at reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated to an oil which
  6. additionwas treated with water
  7. temperaturecooled in the refrigerator
  8. filtrationThe resultant solid was filtered
  9. customtriturated with ether-hexane
  10. filtrationfiltered again

Sources & evidence

ORD record
ord-0853ba5d417d452bad20a32f4e68e5ae
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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