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

Potassium Carbonate → (3-Cyano-3-butene-1-yl)(ethoxycarbonyl)azanyl 1,1-dimethylethyl carbonate

HRID 75178
Notes
Print preview

Reaction equation

HRID 75178 reaction equation
CS(O[CH2:6][CH2:7][CH:8]([CH2:11]O)[C:9]#[N:10])(=O)=O.[C:13](=[O:26])([O:19][NH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])ON(C(C)(C)C)C(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:13](=[O:26])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[O:19][N:20]([CH2:6][CH2:7][C:8]([C:9]#[N:10])=[CH2:11])[C:21]([O:23][CH2:24][CH3:25])=[O:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 866744704-Methylsulfonyloxy-2-(hydroxymethyl) butanenitrile2×HCID 866744711,1-Dimethylethyl (ethoxycarbonyl)azanyl carbonateHCID 866744721,1-Dimethylethyl(ethoxycarbonyl)azanyl carbonate

Product 1

HCID 86674469(3-Cyano-3-butene-1-yl)(ethoxycarbonyl)azanyl 1,1-dimethylethyl carbonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methylsulfonyloxy-2-(hydroxymethyl) butanenitrile (i.e. the product of Step E) (6.87 g, 0.039 mol), 1,1-dimethylethyl (ethoxycarbonyl)azanyl carbonate (7.65 g, 0.037 mol) (i.e. the product of Step F) and potassium carbonate (10.21 g, 0.074 mol) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 20 h. The reaction mixture was poured onto iced water (100 mL) and extracted with diethyl ether (3×50 mL). The combined organic layers were washed with water (50 mL) and concentrated to a pale-tan oil (10.05 g). The oil was adsorbed onto Celite® (diatomaceous filter aid), and then purified by silica gel chromatography (0-100% gradient of ethyl acetate in petroleum ether as eluant). The appropriate fractions were combined to provide the title compound as a yellow oil (3.78 g).

Workup

  1. extractionextracted with diethyl ether (3×50 mL)
  2. washThe combined organic layers were washed with water (50 mL)
  3. concentrationconcentrated to a pale-tan oil (10.05 g)
  4. custompurified by silica gel chromatography (0-100% gradient of ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-b33f2e5e72ee4041adbf8b4167d0f42f
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835427B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes