Diisopropylethylamine → HCID 68851718, compound
Reaction equation
[C:1]([N:10]1[C@@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][O:12][C:11]1=[O:22])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].C(N(C(C)C)CC)(C)C.[O:32]1[CH2:37]CCOO1>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:32][CH2:37][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8])[C:1]([N:10]1[C@@H:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][O:12][C:11]1=[O:22])=[O:9]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (4S)-3-(7-octenoyl)-4-benzyl-1,3-oxazolidin-2-one (2.24 g, 7.59 mmol) and titanium (IV) chloride (1M in dichloromethane, 8.0 mL, 7.97 mmol) in dichloromethane (35 mL) at 0° C. was added dropwise diisopropylethylamine (1.5 mL, 8.35 mmol). After stirring at 0° C. for 1 hour, the resulting titanium enolate was then reacted with a solution of trioxane (0.82 g, 9.11 mmol) in dichloromethane (7 mL), followed by the addition of a solution of titanium (IV) chloride (1M in dichloromethane, 8.0 mL, 7.97 mmol). The reaction mixture was then stirred at 0° C. for 4 h. The reaction mixture was then quenched with saturated ammonium chloride (50 mL). The aqueous layer was extracted with dichloromethane (100 mL×2). The organic extracts were washed with brine, and dried over MgSO4, filtered and concentrated in vacuo to yield the title compound. MH+332.
Workup
- stirringThe reaction mixture was then stirred at 0° C. for 4 h
- customThe reaction mixture was then quenched with saturated ammonium chloride (50 mL)
- extractionThe aqueous layer was extracted with dichloromethane (100 mL×2)
- washThe organic extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5618ccfe2b564a5899e37e16dbe9e3fd
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507726B2
Reaction notes
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