Hydrochloric Acid → HCID 86721099, compound
Reaction equation
C([Mg]Br)C=C.[Cl:6][C:7]1[C:12]([F:13])=[C:11]([C@H:14]([NH:18][S@@](C(C)(C)C)=O)[CH2:15][CH:16]=[CH2:17])[CH:10]=[CH:9][N:8]=1.ClC1[C:31](F)=[C:30]([C@@H:33](N[S@@](C(C)(C)C)=O)[CH2:34][CH:35]=[CH2:36])C=CN=1.Cl.[O:45]1[CH2:50]COCC1.C1C[O:54]CC1>CO>[Cl:6][C:7]1[C:12]([F:13])=[C:11]([C@H:14]([NH:18][C:50](=[O:45])[O:54][C:31]2[CH:30]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:15][CH:16]=[CH2:17])[CH:10]=[CH:9][N:8]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of Intermediate 24A (1.13 g, 4.30 mmol) in THF (50 mL) at was −78° C. was added allylmagnesium bromide (1 M in ether) (8 mL, 8.00 mmol). The reaction was stirred at −78° C. for 0.5 h and warmed up to rt. The mixture was stirred for 1 h at rt and quenched with saturated NH4Cl. The mixture was extracted with EtOAc (3×). The combined organic layer was concentrated to give a 5:1 mixture of (R)—N—((R)-1-(2-chloro-3-fluoropyridin-4-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide and (R)—N—((S)-1-(2-chloro-3-fluoropyridin-4-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide (1.56 g, 119%) as an orange oil. The oil was taken up with methanol (10.00 mL) and treated with 4 N HCl in dioxane (3 mL, 99 mmol). The reaction was stirred at rt for 1.5 h and then concentrated to give the desired product (0.55 g, 40%) as an orange oil. MS (ESI) m/z: 321.1 (M+H)+.
Workup
- customat was −78° C.
- temperaturewarmed up to rt
- stirringThe mixture was stirred for 1 h at rt
- customquenched with saturated NH4Cl
- extractionThe mixture was extracted with EtOAc (3×)
- concentrationThe combined organic layer was concentrated
- customto give
- stirringThe reaction was stirred at rt for 1.5 h
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2c1dfd5c766b4e5285636f4ce279f4eb
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901115B2
Reaction notes
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