Water → HCID 67232369, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([NH:15][CH2:16][CH2:17][NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12][N:11]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:39](=O)(OC(Cl)(Cl)Cl)[O:40]C(Cl)(Cl)Cl.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([N:15]3[CH2:16][CH2:17][N:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:39]3=[O:40])[CH2:13][CH2:12][N:11]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the compound (0.21 g) obtained in step 3 and triethylamine (0.19 mL) in THF (10 mL) was added bis(trichloromethyl) carbonate (0.13 g) at 5° C. The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 1 hr, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 10→33% ethyl acetate/hexane) to give the title compound (0.04 g, 18%) as a colorless oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
- customdried
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (solvent gradient; 10→33% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-bea46a30401546bab5ad9eb57a3b1c9b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592454B2
Reaction notes
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