Tetrahydrofuran → HCID 66775914, compound
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12](CC(C)C)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]C[CH2:21][CH2:22][CH3:23].C([O:27][B:28](OC(C)C)[O:29]C(C)C)(C)C.[CH2:37]1COCC1>>[CH2:37]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([S:6]([NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:7])=[O:8])[C:14]=1[B:28]([OH:29])[OH:27])[CH:22]([CH3:21])[CH3:23]Participants
Conditions
- Temperature
- -40 °C
Procedure
To a solution of N-tert-butyl-4-iso-butyl-benzenesulfonamide (2.69 g, 10 mmol, see step (a)) in THF (50 mL), n-BuLi (15.6 mL, 1.6M, 25 mmol) was added dropwise at −78° C. under an atmosphere of N2 (g). The temperature was allowed to rise gradually to 0° C. over 2 h and was then kept at that temperature for 30 min. The reaction mixture was then cooled to −40° C. and tri-iso-propylborate (4.6 mL, 20 mmol) was added. The reaction mixture was stirred overnight at ambient temperature and was quenched with 2M HCl (20 mL). The organic phase was separated and the water phase was extracted with EtOAc (3×100 mL). The combined organic phase was washed with brine and dried and concentrated in vacuo. The crude product was used in the next step without further purification.
Workup
- waitwas then kept at that temperature for 30 min
- customwas quenched with 2M HCl (20 mL)
- customThe organic phase was separated
- extractionthe water phase was extracted with EtOAc (3×100 mL)
- washThe combined organic phase was washed with brine
- customdried
- concentrationconcentrated in vacuo
- customThe crude product was used in the next step without further purification
Sources & evidence
- ORD record
- ord-5396517a0d894e568572922e7843e0b6
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124638B2
Reaction notes
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