tert-Butyl 3-ethynylphenylcarbamate → tert-Butyl {3-[(5-nitro-2-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-2,3-dihydro-1,3-benzoxazol-7-yl)ethynyl]phenyl}carbamate
Reaction equation
I[C:2]1[C:10]2[O:9][C:8](=[O:11])[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[CH:5]=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.[C:23]([C:25]1[CH:26]=[C:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:28]=[CH:29][CH:30]=1)#[CH:24]>>[N+:20]([C:4]1[CH:3]=[C:2]([C:24]#[C:23][C:25]2[CH:26]=[C:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH:28]=[CH:29][CH:30]=2)[C:10]2[O:9][C:8](=[O:11])[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[CH:5]=1)([O-:22])=[O:21]Participants
3
Procedure
The desired compound was prepared according to the procedure of Example B5, step C, using 7-iodo-5-nitro-3-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-benzoxazol-2(3H)-on and tert-butyl (3-ethynylphenyl)carbamate as the starting materials in quantitative yield. LCMS for C26H31N3O7SiNa (M+Na)+: m/z=548.0.
Sources & evidence
- ORD record
- ord-71bf2031817c498ab61dce68f57a2b82
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
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