Thionyl Chloride → HCID 89533691, compound
Reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[O:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 1.50 g (8.10 mmol; 1.0 eq) of 2-fluoro-3-nitrobenzoic acid and 16 ml of thionyl chloride was refluxed for 3 hours. The excess thionyl chloride was then concentrated and the residue was co-evaporated twice with toluene. The resulting acid chloride was taken up in 25 ml of dichloromethane. 1.27 g (8.10 mmol; 1.0 eq) of isopropyl (S)-pyrrolidine-2-carboxylate were added to this mixture cooled to 0° C. The reaction medium was stirred at 0° C. for 30 minutes and then at ambient temperature for 2 hours. The reaction medium was diluted and washed with a 1 M hydrochloric acid solution (100 ml) and then with a saturated sodium hydrogen carbonate solution (100 ml). The organic phase was dried over MgSO4, filtered and evaporated. 2.12 g of isopropyl (S)-1-(2-fluoro-3-nitrobenzoyl)pyrrolidine-2-carboxylate were obtained. Yield=81%.
Workup
- temperaturewas refluxed for 3 hours
- concentrationThe excess thionyl chloride was then concentrated
- waitat ambient temperature for 2 hours
- additionThe reaction medium was diluted
- washwashed with a 1 M hydrochloric acid solution (100 ml)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-adc285fdcd09451abfccc72be174b16f
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388149B2
Reaction notes
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