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

N-Hydroxysuccinimide → 2,5-Dioxopyrrolidin-1-yl 2-methoxyacetate

HRID 1753109
Notes
Print preview

Reaction equation

HRID 1753109 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[OH:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14].C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][O:2][CH2:3][C:4]([O:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 96623Methoxyacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 103524272,5-Dioxopyrrolidin-1-yl 2-methoxyacetateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methoxyacetyl chloride (108.5 g, 1 mol) in absolute dichloromethane (170 mL) was added dropwise at 0° C. to a solution of N-hydroxysuccinimide (115 g, 1 mol) and TEA (111 g, 1 mol) in dichloromethane (900 mL). The reaction mixture was stirred at room temperature for 48 hours, and a saturated NaHCO3 solution (500 mL) was added under stirring. The organic layer was separated, and the aqueous layer was subjected to extraction twice with chloroform. The combined organic extract was washed with saturated NaHCO3 solution (200 mL), brine (200 mL), and dried over Na2SO4. The solution was concentrated in vacuo to afford the title compound as a yellow oil (147.8 g, 79%). Taken directly on to the next step.

Workup

  1. stirringunder stirring
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was subjected to extraction twice with chloroform
  4. extractionThe combined organic extract
  5. washwas washed with saturated NaHCO3 solution (200 mL), brine (200 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6845c8b53cd246d0a9c7c12ce0acc910
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09163021B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes