Diisopropylethylamine → HCID 22062708, compound
Reaction equation
[CH2:1]([O:17]CCCOS(C)(=O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 97.5 °C
Procedure
Substitution of (32) with Bz-c-CDV. 1.7 g (4.6 mmol) of Bz-c-CDV was dissolved in 10 mL of NMP and 1.2 mL (7 mmol) of DIPEA was added to it followed by 9 g (23.9 mmol) of 32. The reaction was heated at 95-100° C. for 24 h at which time the TLC showed the product together with some Bz-c-CDV. At this stage the reaction was allowed to proceed for an additional 4 h, but as the TLC did not show much progress, the reaction mixture was cooled to room temperature and the solvent was evaporated under high vacuum. The residue was purified by combiflash using chloroform/MeOH as eluent to furnish 1.33 g of target product 26 as yellow oil in 45% yield.
Workup
- temperaturethe reaction mixture was cooled to room temperature
- customthe solvent was evaporated under high vacuum
- customThe residue was purified by combiflash
Sources & evidence
- ORD record
- ord-692d59e80f3340618f8b5d3fa4813199
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07749983B2
Reaction notes
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