Dichloromethane → HCID 59128572, compound
Reaction equation
[K+].[CH3:2][Si:3]([CH3:17])([CH3:16])[CH2:4][CH2:5][O:6][CH2:7][N:8]1[CH:12]=[N:11][C:10]([C:13]([O-:15])=O)=[N:9]1.CC[N:20]([CH:24]([CH3:26])C)[CH:21]([CH3:23])C.FC(F)(F)[C:29]([OH:31])=[O:30].[C:34]1([C:40]2[CH:45]=[C:44]([CH:46]3CCNCC3)[CH:43]=[CH:42][C:41]=2[NH:52]C(C2NC=C(C#N)N=2)=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=1.C1CN([P+](Br)(N2[CH2:77][CH2:76][CH2:75]C2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:86](Cl)Cl>>[C:76]([O:31][C:29]([N:20]1[CH2:21][CH2:23][CH:46]([C:44]2[CH:43]=[CH:42][C:41]([NH:52][C:13]([C:10]3[N:11]=[CH:12][N:8]([CH2:7][O:6][CH2:5][CH2:4][Si:3]([CH3:2])([CH3:17])[CH3:16])[N:9]=3)=[O:15])=[C:40]([C:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=3)[CH:45]=2)[CH2:26][CH2:24]1)=[O:30])([CH3:75])([CH3:77])[CH3:86]Participants
Reactant 5
Product 1
Procedure
A mixture of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-[1,2,4]-triazole-3-carboxylic acid potassium salt (as prepared above, 28 mg, 0.10 mmol), DIEA (34 μL, 0.20 mmol), 4-(4-amino-3-cyclohex-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in Example 14, step (b), 35.6 mg, 0.100 mmol) and PyBroP (69.9 mg, 0.150 mmol) in DCM (2 mL) was stirred at RT for 12 h. The reaction mixture was diluted with DCM (5 mL) and washed with saturated aqueous NaHCO3 (10 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The product was chromatographed on silica (20-40% EtOAc/hexane) to obtain the title compound (31.9 mg, 55%). Mass spectrum (ESI, m/z): Calcd. for C31H47N5O4Si, 481.2 (M-BOC+2H). found. 481.2.
Workup
- washwashed with saturated aqueous NaHCO3 (10 mL) and water (10 mL)
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe product was chromatographed on silica (20-40% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-c80777318c4543e590a08a020b2101cc
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557847B2
Reaction notes
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