Triethylamine → HCID 21968719, compound
Reaction equation
[O:1]=[C:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=O.CCN(CC)CC.C(Cl)(=O)C(C)(C)C.[CH2:25]([C@H:32]1[CH2:36][O:35][C:34](=[O:37])[NH:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Li]CCCC.[Li]>C(OCC)(=O)C.C1COCC1>[CH2:25]([C@H:32]1[CH2:36][O:35][C:34](=[O:37])[N:33]1[C:7](=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH3:10])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 6-oxo-heptanoic acid 7-1 (100 g, 694 mmol), NEt3 (111.3 ml, 763.4 mmol) and THF (2000 mL) at −78° C. was added pivaloyl chloride (98.7 ml, 763.4 mmol). 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 (136 g, 763.4 mmol) and THF (2000 ml) at −78° C. was added nBuLi (306 ml, 765 mmol, 2.5M in hexanes) dropwise over 30 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 20 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was azeotroped with xylenes to give 7-2 as a colorless foam.
Workup
- customrecooled to −78° C
- waitAfter 20 minutes
- temperaturethe reaction was warmed to 0° C. for 1.0 h
- washwashed with sat. NaHCO3, brine
- dry with materialdried over MgSO4
- customremoval of the solvent
- customthe residue was azeotroped with xylenes
Sources & evidence
- ORD record
- ord-565a92bb57af4db4934774dca035c161
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268378B1
Reaction notes
Loading…