Triethylamine → HCID 11437716, compound

HRID 2227261Notes

Reaction equation

HRID 2227261 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]([OH:9])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH2:24]([C@H:31]1[CH2:35][O:34][C:33](=[O:36])[NH:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Li]CCCC.[Li]>O1CCCC1.C(OCC)(=O)C>[CH2:24]([C@H:31]1[CH2:35][O:34][C:33](=[O:36])[N:32]1[C:7](=[O:9])[CH2:6][CH2:5][CH2:4][C:1](=[O:3])[CH3:2])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 184074-Acetylbutyric acidHCID 62493Pivaloyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 11437716HCID 11437716, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-acetylbutyric acid 1-7 (25.0 g, 192 mmol), triethylamine (29.5 ml, 211 mmol) in tetrahydrofuran (500 mL) at −78° C. was added pivaloyl chloride (26.0 ml, 211 mmol). After 20 min, the mixture was warmed to 0° C. for 1.0 h and then recooled to −78° C. To a stirred solution of (S)-(−)-4-benzyl-2-oxazolidinone (37.4 g, 211 mmol) in tetrahydrofuran (500 ml) at −78° C. was added nBuLi (84.5 ml, 211 mmol, 2.5M in hexanes) dropwise over 10 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 10 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure to give 1-8 as a solid which was triturated with ethyl ether and filtered to give a white solid.

Workup

  1. customrecooled to −78° C
  2. waitAfter 20 minutes
  3. waitAfter 10 minutes
  4. temperaturethe reaction was warmed to 0° C. for 1.0 h
  5. washwashed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe reaction mixture was filtered
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-a32f826d55b445fd9b9c5ee8c7c91e45
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

Loading…