Sodium Hydroxide → HCID 19389003, compound

HRID 1110318Notes

Reaction equation

HRID 1110318 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]([S:31]([CH3:33])=[O:32])[CH:7]=1.[OH-].[Na+]>CO>[C:35]([CH2:34][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]([S:31]([CH3:33])=[O:32])[CH:7]=1)[CH2:4][C:3]([OH:39])=[O:2])([OH:37])=[O:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19389020HCID 19389020, compound

Product 1

HCID 19389003HCID 19389003, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.53 g (0.93 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3-(methylsulfinyl)-5-(octadecyloxy)phenyl]glycine methyl ester and 0.8 ml (4.7 mmol) of 6 N NaOH in 40 ml of methanol was stirred at reflux under argon for 6 hours. The solvent was removed at reduced pressure, the residue was acidified and the product was extracted with 10% THF-ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from THF-ethyl acetate to give 0.42 g (84% yield), mp 147°-149°, of N-(carboxymethyl)-N-[3-(methylsufinyl)-5-(octadecyloxy)phenyl]glycine.

Workup

  1. temperatureat reflux under argon for 6 hours
  2. customThe solvent was removed at reduced pressure
  3. extractionthe product was extracted with 10% THF-ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated to a solid which
  6. customwas recrystallized from THF-ethyl acetate
  7. customto give 0.42 g (84% yield), mp 147°-149°

Sources & evidence

ORD record
ord-8583d72146774b518cb7c0066f11e0f1
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

Loading…