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

Methyl iodide → HCID 86658011, compound

HRID 70654
Notes
Print preview

Reaction equation

HRID 70654 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:32]2[CH:37]=[CH:36][C:35]([CH:38]([OH:40])[CH3:39])=[C:34]([O:41][CH3:42])[N:33]=2)=[CH:14]\[C@@H:15]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[O:29][CH3:30])[C:18](=[O:31])[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[C:43](=[S:45])=[S:44].[CH3:46]I>O1CCCC1.O>[C:43]([S:45][CH3:46])(=[S:44])[O:40][CH:38]([C:35]1[C:34]([O:41][CH3:42])=[N:33][C:32](/[C:13](/[C:10]2[CH:11]=[CH:12][C:7]([C:3]([CH3:4])([CH3:5])[CH3:6])=[CH:8][CH:9]=2)=[CH:14]/[C@H:15]2[CH2:16][CH2:17][C:18](=[O:31])[N:19]2[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])=[CH:37][CH:36]=1)[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 67399360HCID 67399360, compound

Product 1

HCID 86658011HCID 86658011, compound

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (22 mg, 60% in oil) was added to a solution of (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(1-hydroxyethyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (100 mg) in tetrahydrofuran (2 mL) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. The reaction solution was warmed to room temperature and carbon disulfide (66.7 μL) was added, followed by stirring for 30 minutes. Methyl iodide (68.5 μL) was added and the mixture was stirred for 3.5 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1) to give O-[1-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)ethyl] S-methyl carbonodithioate as a colorless oil (109 mg).

Workup

  1. temperaturecooling
  2. stirringby stirring for 30 minutes
  3. stirringthe mixture was stirred for 3.5 hours
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-b9b5f7c360c04693889890bd96412fb1
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822503B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes