Hydrochloric Acid → HCID 178485441, compound
Reaction equation
C[C:2]1[C:10]([S:11][C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][C:17](=[O:21])[NH:18]3)=[CH:14][CH:13]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:22](OCC)=[O:23].[O-][CH2:28]C.[Na+].Cl>C(O)C.CCOC(C)=O>[OH:23][CH:22]=[C:16]1[C:15]2[C:19](=[CH:20][C:12]([S:11][C:10]3[CH:2]=[C:3]([CH:7]=[CH:8][CH:9]=3)[C:4]([NH:6][CH3:28])=[O:5])=[CH:13][CH:14]=2)[NH:18][C:17]1=[O:21]Participants
Conditions
- Temperature
- 78 °C
Procedure
Methyl-3-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide (as prepared in step 1 above; 0.71 g, 0.239 mmol) and ethyl formate (0.058 mL, 0.717 mmol) were dissolved in anhydrous ethanol (0.5 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (0.446 mL, 1.20 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH=1 with dropwise addition of 1M HCl(aq). The reaction mixture was diluted with EtOAc (15 mL) and washed with brine (3×15 mL). The combined organics were then dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified via flash silica gel chromatography (10% MeOH in CHCl3) affording the title compound in 26% yield (0.020 g, 0.0621 mmol).
Workup
- customproducing a black oil
- temperatureSubsequently, the reaction mixture was cooled to room temperature
- washwashed with brine (3×15 mL)
- dry with materialThe combined organics were then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified via flash silica gel chromatography (10% MeOH in CHCl3)
Sources & evidence
- ORD record
- ord-8fe67a9d02e04ac995dc9fc3b28539dd
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07439371B2
Reaction notes
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