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N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

HRID 30490
Notes
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Reaction equation

HRID 30490 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:21])[O:8][C:9]([C:14](=[O:20])[N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])([CH2:12][CH3:13])[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH3:22][N:23]([CH:25](N(C)C)N(C)C)[CH3:24]>CN(C)C=O.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:21])[O:8][C:9]([C:14](=[O:20])[N:15]([CH2:16][CH3:17])[CH2:18][CH3:19])([CH2:12][CH3:13])[C:10]=1/[CH:11]=[CH:22]/[N:23]([CH3:25])[CH3:24])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 674534935-Diethylcarbamoyl-5-ethyl-4-methyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

Product 1

HCID 866073575-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl esterYield 90.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 500.0 mg of compound (12) as obtained from example 5 (22.73 mmol) in 3.0 mL dimethyl formamide were added at room temperature 3.0 mL tris(dimethylamino)methane (17.3 mmol, 10.3 eq). The color of the reaction mixture changed from orange to brown and further to green. After 17 h, the mixture was diluted with 50 mL dichloromethane, washed with 25mL aqueous hydrochloric acid (1.0 M) and washed again three times with 50 mL brine. The organic phase was dried over 2 g sodium sulfate and was filtered. The filter cake was washed with 4 mL dichloromethane. After evaporation of the solvent in a rotary evaporator (50° C., 5 mbar), the crude product was obtained as an orange oil (627.0 mg, 106% by weight), which was liberated from residual dimethyl formamide in a high vacuum rotary evaporator (50° C., 0.5 mbar) yielding the title product (536.0 mg, 1.517 mmol, 90% by weight) as orange crystals.

Workup

  1. washwashed with 25mL aqueous hydrochloric acid (1.0 M)
  2. washwashed again three times with 50 mL brine
  3. dry with materialThe organic phase was dried over 2 g sodium sulfate
  4. filtrationwas filtered
  5. washThe filter cake was washed with 4 mL dichloromethane
  6. customAfter evaporation of the solvent
  7. customin a rotary evaporator (50° C., 5 mbar)
  8. customthe crude product was obtained as an orange oil (627.0 mg, 106% by weight), which
  9. customwas liberated from residual dimethyl formamide in a high vacuum rotary evaporator (50° C., 0.5 mbar)

Sources & evidence

ORD record
ord-2407a8bc04a94897837d24baff3ecaa2
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423152B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes