Methanesulfonyl chloride → HCID 68577068, compound
Reaction equation
C([N:8]1[CH2:31][CH2:30][C@@:15]23[C:16]4[CH:17]=[C:18]([O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][C:21]=4[CH2:22][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)(OC(C)(C)C)=O.O1CCOCC1.Cl.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([N:8]1[CH2:31][CH2:30][C@@:15]23[C:16]4[CH:17]=[C:18]([O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][C:21]=4[CH2:22][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)(=[O:42])=[O:41]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of compound 31 (5 mg, 0.012 mmol) in dry CH2Cl2 (0.2 mL) was added 4 M HCl dioxane solution (0.5 mL) and stirred for 2 h at 0° C. The solvent was evaporated under reduced pressure. The crude amine salt 32 was dissolved in CH2Cl2 (0.5 mL) and slowly added methanesulfonyl chloride (2 μL, 0.030 mmol) and TEA (9 μL, 0.064 mmol) at 0° C. After 1 h stirring, the reaction mixture was concentrated under reduced pressure. The crude product was purified on a silica gel column chromatography (3:1 n-Hexane/EtOAc) to give a colorless oil (3 mg, 82% yield): 1H NMR (300 MHz, CDCl3) 1.08˜1.87 (m, 20H); 2.36 (d, J=12.4 Hz, 1H); 2.77˜2.92 (m, 5H); 3.51˜3.54 (m, 1H); 4.10˜4.15 (m, 1H); 6.86˜6.96 (m, 2H); 7.13 (d, J=8.3 Hz, 1H).
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionThe crude amine salt 32 was dissolved in CH2Cl2 (0.5 mL)
- customat 0° C
- stirringAfter 1 h stirring
- concentrationthe reaction mixture was concentrated under reduced pressure
- customThe crude product was purified on a silica gel column chromatography (3:1 n-Hexane/EtOAc)
Sources & evidence
- ORD record
- ord-b210b5eeec3942e0bedd00958cdf4bdb
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691874B2
Reaction notes
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