Boron Trichloride → HCID 76903235, compound
Reaction equation
CC12[O:10][B:9]([C@@H:11]([NH:28][C:29]([C:31]3([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:33][CH2:32]3)=[O:30])[CH2:12][C:13]3[C:14](OC)=[C:15]([CH:23]=[CH:24][CH:25]=3)[C:16]([O:18]C(C)(C)C)=[O:17])[O:8]C1CC1CC2C1(C)C.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:8][B:9]1[C@@H:11]([NH:28][C:29]([C:31]2([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:32][CH2:33]2)=[O:30])[CH2:12][C:13]2[CH:25]=[CH:24][CH:23]=[C:15]([C:16]([OH:18])=[O:17])[C:14]=2[O:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 3-((2R)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-2-(1-phenylcyclopropanecarboxamido)ethyl)-2-methoxybenzoate from step 1 (200 mg, 0.35 mmol) in anhydrous CH2Cl2 (5 mL) at −78° C. was added BCl3 (2.5 mL, 1M in DCM, 2.5 mmol), and the reaction mixture was stirred at same temperature for 1 hr, at which time the reaction mixture was warmed up to 0° C. and stirred at same temperature for additional 1 hr. The reaction was quenched by addition of water (5 mL) at 0° C. The aqueous phase was extracted by EtOAc. The organic phase was washed with brine, dried over Na2SO4, and concentrated. The crude product was recrystallized in EtOAc/Hexane to afford the product (35 mg) as white solid. ESI-MS m/z 352 (MH)+.
Workup
- stirringstirred at same temperature for additional 1 hr
- customThe reaction was quenched by addition of water (5 mL) at 0° C
- extractionThe aqueous phase was extracted by EtOAc
- washThe organic phase was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe crude product was recrystallized in EtOAc/Hexane
Sources & evidence
- ORD record
- ord-df2daa49da584aa2a12d856f819e37dc
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403850B2
Reaction notes
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