Triethylamine → HCID 10344934, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=2)[N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH:42]1([C:48](Cl)=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl.CN(C1C=CN=CC=1)C>[CH:42]1([C:48]([NH:1][C:2]2[CH:3]=[C:4]([C@@H:8]([N:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=3)[CH:5]=[CH:6][CH:7]=2)=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1Participants
Procedure
To a room temperature solution of INTERMEDIATE 5a (250 mg; 0.54 mmol) in dichloromethane (5 mL) were added triethylamine (0.15 mL; 1.08 mmol), DMAP (cat.) and cyclohexane carbonyl chloride (86 μL; 0.64 mmol). The reaction mixture was stirred for 5 hours then more triethylamine (0.08 mL; 0.58 mmol) and DMAP (cat.) were added. The reaction mixture was stirred overnight then more cyclohexane carbonyl chloride (28 μL; 0.21 mmol) was added. The reaction mixture stirred for 5 hours then was washed with two portions of saturated sodium bicarbonate. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography eluting with 2% methanol in dichloromethane gave the desired product.
Workup
- stirringThe reaction mixture was stirred overnight
- stirringThe reaction mixture stirred for 5 hours
- washthen was washed with two portions of saturated sodium bicarbonate
- dry with materialThe organic phase was dried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- washColumn chromatography eluting with 2% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-636e91d6a826413f86153561753a6258
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241764B2
Reaction notes
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