Diethylamine → HCID 45111295, compound
Reaction equation
[CH3:1][C:2]1([C:7]([OH:9])=O)[CH2:6][S:5][S:4][CH2:3]1.C(Cl)(=O)C(Cl)=O.[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17].C(N(C(C)C)CC)(C)C>ClCCl.CCCCCCC.CCOC(C)=O.CN(C=O)C>[CH2:16]([N:18]([CH2:19][CH3:20])[C:7]([C:2]1([CH3:1])[CH2:6][S:5][S:4][CH2:3]1)=[O:9])[CH3:17]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
5 ml of anhydrous dichloromethane and 0.1 ml of anhydrous DMF are added to 2.26 mmol of Compound 1. The mixture is cooled to 0° C. and 2.7 mmol of oxalyl chloride are added. The mixture is stirred at 20° C. and then added at 0° C. to a mixture of 2.26 mmol of diethylamine, 5 ml of anhydrous dichloromethane and 6.8 mmol of diisopropylethylamine. The reaction medium is stirred for 3 hours at 20° C. When the reaction is complete, the medium is diluted in 50 ml of dichloromethane and then washed with 2×30 ml of water and 1×50 ml of saturated NH4Cl solution, dried over Na2SO4 and evaporated to dryness on a rotavapor. After flash chromatography (eluent: heptane/EtOAc), Compound 18 is isolated in the form of a yellow oil (48% yield).
Workup
- stirringThe reaction medium is stirred for 3 hours at 20° C
- washwashed with 2×30 ml of water and 1×50 ml of saturated NH4Cl solution
- dry with materialdried over Na2SO4
- customevaporated to dryness on a rotavapor
Sources & evidence
- ORD record
- ord-91ea94b8d4124a3dbed2cbc620bf0ce1
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08617524B2
Reaction notes
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