HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Iodide → HCID 19389004, compound

HRID 1757869
Notes
Print preview

Reaction equation

HRID 1757869 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][N:5]([C:11]1[CH:16]=[C:15]([O: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][CH2:32][CH2:33][CH2:34][CH3:35])[CH:14]=[C:13]([OH:36])[CH:12]=1)[CH2:6][C:7]([O:9][CH3:10])=[O:8].Cl.Cl[CH2:40][C:41]1[CH:50]=[CH:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:42]=1.C(=O)([O-])[O-].[I-].[Na+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:37])[CH2:4][N:5]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:11]1[CH:12]=[C:13]([O:36][CH2:40][C:41]2[CH:50]=[CH:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[N:42]=2)[CH:14]=[C:15]([O: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][CH2:32][CH2:33][CH2:34][CH3:35])[CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 19660Carbonate IonHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 19388979N-(2-methoxy-2-oxoethyl)-N-[3-hydroxy-5-(octadecyloxy)phenyl]glycine methyl ester

Product 1

HCID 19389004HCID 19389004, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (2.9 mmol) of N-[3-hydroxy-5-(octadecyloxy)phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester, 0.935 g (4.35 mmol) of 2-(chloromethyl)quinoline hydrochloride (Lancaster Organic Research Chemicals), 2.0 g (14.5 mmol) ofpotassium carbonate and 0.435 g (2.9 mmol) of sodium iodide in 100 ml of acetone and 20 ml of DMF was stirred at reflux under argon for 24 hours. The solvents were removed at reduced pressure and the residue was treated with water and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was purified by HPLC using 30% ethyl acetate-hexane followed by recrystallization from hexane to give 1.5g (78% yield, mp 76°-79°) of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-[(2-quinolinyl)methoxy]phenyl]glycine methyl ester.

Workup

  1. temperatureat reflux under argon for 24 hours
  2. customThe solvents were removed at reduced pressure
  3. additionthe residue was treated with water
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by HPLC
  8. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-6eda6c89a0fa417287e8de488c770b28
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05446189

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes