Triethylamine → HCID 11748816, compound

HRID 1096183Notes

Reaction equation

HRID 1096183 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>CCO>[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 EtOH (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 EtOH (20 ml). The ice bath was removed and the reaction allowed to reach RT. After 2 h of stirring the reaction was concentrated, the residue redissolved in CH2Cl2, washed with sat. aq. NaHCO3 solution, dried (Na2SO4) and concentrated affording (S)-4-bromo-3-methyl-butyric acid ethyl ester (33.6 g, quant). This was redissolved in EtOH (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 CH2Cl2, washed with sat. aq. NaHCO3 solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc/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 CH2Cl2
  4. washwashed with sat. aq. NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (EtOAc/heptane 5:95)

Sources & evidence

ORD record
ord-71c5ef02b4424b12905e122d282bd159
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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