Methanol → HCID 86754535, compound

HRID 619011Notes

Reaction equation

HRID 619011 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:6][C:7](=[O:10])[O:8][CH3:9].C[O-].[Na+].[CH3:20][C:21](=[CH:23][CH2:24][CH2:25]/[C:26](=[CH:28]/CO)/[CH3:27])[CH3:22].CO>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][N:5]([CH2:4][C:3]([O:2][CH2:1]/[CH:28]=[C:26](/[CH2:25][CH2:24][CH:23]=[C:21]([CH3:20])[CH3:22])\[CH3:27])=[O:16])[CH2:6][C:7](=[O:10])[O:8][CH2:9]/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22])/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])\[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 637566GeraniolHCID 10942334Sodium MethoxideHCID 14440960Trimethyl 2,2',2''-nitrilotriacetate

Product 1

HCID 86754535HCID 86754535, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of N,N-bis(2-methoxy-2-oxoethyl)glycine methyl ester (7.0 g, 30 mmol, 1 eq) in toluene (80 ml) under argon was slowly added some sodium methoxide (0.49 g, 0.009 mol, 3*0.10 eq) and geraniol (14.57 g, 95 mmol, 3*1.05 eq). The mixture was heated under vacuum (10 mm Hg) and the methanol produced by the transesterification reaction is distilled with toluene over two hours after which the reaction appeared completed by 1H NMR. Any remaining toluene is evaporated under vacuum. Diethyl ether was added (200 ml) and the mixture stored at 4° C. for one hour prior to filtration. The filtrate was then concentrated under vacuum yielding to the expected N,N-bis(2-geranyloxy-2-oxoethyl)glycine geranyl ester as a yellow oil (quantitative yield).

Workup

  1. temperatureThe mixture was heated under vacuum (10 mm Hg)
  2. distillationis distilled with toluene over two hours after which the reaction
  3. customAny remaining toluene is evaporated under vacuum
  4. additionDiethyl ether was added (200 ml)
  5. filtrationto filtration
  6. concentrationThe filtrate was then concentrated under vacuum

Sources & evidence

ORD record
ord-646e98aac5474ddabfcb0a94369c1624
Source dataset
uspto-grants-1999_09
Patent number
US05958870

Reaction notes

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