Triethylamine → HCID 11748816, compound

HRID 655500Notes

Reaction equation

HRID 655500 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C(N([CH2:20][CH3:21])CC)C>C(O)C>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C@@H:20]([N:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH3:21])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 80908N-Benzylglycine ethyl ester

Product 1

HCID 11748816HCID 11748816, compoundYield 41,275.602%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To ethanol (55 ml) cooled to 0° C. was added acetyl bromide (41 ml, 0.6 mol) dropwise, followed by a solution of (S)-4-methyl-dihydro-furan-2-one (Tetrahedron 1983, 39, 3107; 18.6 g, 0.2 mol) in ethanol (20 ml). The ice bath was removed and the reaction allowed to reach room temperature. After 2 h of stirring the reaction was concentrated, the residue redissolved in dichloromethane, washed with sat. aq. sodium hydrogencarbonate solution, dried (Na2SO4) and concentrated affording (S)-4-bromo-3-methyl-butyric acid ethyl ester (33.6 g, quantitative). This was redissolved in ethanol (100 ml), cooled to 0° C. and N-benzylglycine ethyl ester (28.2 g, 0.14 mol) and triethylamine (22.4 ml, 0.16 mmol) were added. The reaction was then warmed to 75° C. for 4 d after which time the reaction was concentrated, the residue redissolved in dichloromethane, washed with sat. aq. sodium hydrogencarbonate solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (ethyl acetate/heptane 5:95) afforded the titled product as a light gold oil (20.3 g, 43%). MS (ISP)=322.2 (M+H)+.

Workup

  1. temperatureThe reaction was then warmed to 75° C. for 4 d after which time the reaction
  2. concentrationwas concentrated
  3. dissolutionthe residue redissolved in dichloromethane
  4. washwashed with sat. aq. sodium hydrogencarbonate solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (ethyl acetate/heptane 5:95)

Sources & evidence

ORD record
ord-54b2263b039a422395e8084b0ca45f81
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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