Dimethyl Sulfoxide → HCID 12112437, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:29][OH:30])=[C:16]([NH:18][C:19](=[O:28])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:29]=[O:30])=[C:16]([NH:18][C:19](=[O:28])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a solution of oxalyl chloride (4.46 g, 35.13 mmol) and methylene chloride (300 mL) at −78° C. was added dimethyl sulfoxide (3.29 g, 42.15 mmol) over 15 min. After 15 min at −78° C., a solution of N-[5-fluoro-2-hydroxymethylphenyl]benzenepropanamide from Step 2 (3.20 g, 11.7 mmol) and methylene chloride (300 mL) was added over 10 min. After 45 min at −78° C., triethylamine (8.53 g, 84.3 mmol) was added and the reaction was warmed to 23° C. After 20 min at 23° C., the reaction was washed with sat'd NaHCO3 (2×100 mL), brine (1×100 mL) and dried (MgSO4). After concentration in vacuo, the crude residue was purified by flash chromatography (ethyl acetate:hexane 1:3) which afforded the aldehyde as an oil (2.71 g, 85.4%): 1H NMR (CDCl3) δ 2.79 (t, J=7 Hz), 3.06-3.16 (m), 6.85-6.93 (m), 7.17-7.37 (m), 7.63-7.69 (m), 8.52-8.58 (m), 9.84 (s).
Workup
- waitAfter 45 min at −78° C.
- waitAfter 20 min at 23° C.
- washthe reaction was washed with sat'd NaHCO3 (2×100 mL), brine (1×100 mL)
- dry with materialdried (MgSO4)
- concentrationAfter concentration in vacuo
- customthe crude residue was purified by flash chromatography (ethyl acetate:hexane 1:3) which
Sources & evidence
- ORD record
- ord-e10dcaf0db9f431ba00617b901d97355
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673784B1
Reaction notes
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