Triethylamine → HCID 15521919, compound

HRID 850590Notes

Reaction equation

HRID 850590 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.[CH3:25][NH:26][O:27][CH3:28]>C(Cl)(Cl)Cl>[CH3:28][O:27][N:26]([CH3:25])[C:1](=[O:8])[CH2:2][CH2:3][C:4](=[O:5])[CH3:6]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 11579Levulinic AcidHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 15521919HCID 15521919, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of levulinic acid (30 g, 0.258 mol) in CHCl3 (850 mL) at 0° C. was added triethylamine (43.2 mL, 0.310 mol), followed by isobutyl chloroformate (37 mL, 0.284 mol) over 15 minutes. After 30 minutes, triethylamine (57.6 mL, 0.413 mol) was added, followed by N,O-dimethylhydroxylamine hydrochloride (37.8 g, 0.387 mol) in 5 portions over 5 minutes. Vigorous bubbling ensued, and the mixture was allowed to warm to RT and stirred for 1 h. The mixture was reduced to a moist solid by rotary evaporation under reduced pressure, slurried in 500 mL EtOAc, washed with 10% K2CO3, brine, and dried over Na2SO4. Evaporative removal of the solvent gave 2-1 as a yellow oil. TLC Rf =0.42 (silica,1:1 chloroform/ethyl acetate). 1H MM (300 MHz, CDCl3) δ 3.74 (s, 3H), 3.18 (s, 3H), 2.65-2.95 (m, 4H), 2.21 (s, 3H).

Workup

  1. customVigorous bubbling
  2. customThe mixture was reduced to a moist solid by rotary evaporation under reduced pressure
  3. washwashed with 10% K2CO3, brine
  4. dry with materialdried over Na2SO4
  5. customEvaporative removal of the solvent

Sources & evidence

ORD record
ord-f54e341eb8474b8282f7cf5e629fa0b2
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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