Tetrabutylammonium Fluoride → HCID 145857714, compound
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si](C)(C)CCOC(=O)[NH:25][C:26]1[CH:31]=[C:30]([NH2:32])[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([S:39]([C:42]3[CH:46]=[C:45]([C:47]([NH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[NH:48])[S:44][C:43]=3[S:57][CH3:58])(=[O:41])=[O:40])[CH:34]=2)=[C:28]([CH3:59])[CH:27]=1>C1COCC1>[C:53]([O:52][C:50](=[O:51])[NH:49][C:47]([C:45]1[S:44][C:43]([S:57][CH3:58])=[C:42]([S:39]([C:35]2[CH:34]=[C:33]([C:29]3[C:30]([NH2:32])=[CH:31][C:26]([NH2:25])=[CH:27][C:28]=3[CH3:59])[CH:38]=[CH:37][CH:36]=2)(=[O:40])=[O:41])[CH:46]=1)=[NH:48])([CH3:56])([CH3:55])[CH3:54]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of tetrabutylammonium fluoride (1M in THF, 1 mL, 1 mmol) was added to a solution of {6-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-2-methyl-biphenyl-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester ((Example 294: step f) 86 mg, 0.11 mmol) in THF (1 mL). The solution was heated at 50° C. for 12 h, then the solution was partitioned between EtOAc (50 mL) and water (20 mL). The layers were separated and the organic layer was further extracted with water (5×10 mL) and brine (20 mL). The solution was dried over sodium sulfate and concentrated in vacuo to yield the title compound (71 mg, 84%) which was used without further purification. ESI-MS (m/z): Calcd. for C24H28N4O4S3 (M+H): 533.1; found: 532.7.
Workup
- customthe solution was partitioned between EtOAc (50 mL) and water (20 mL)
- customThe layers were separated
- extractionthe organic layer was further extracted with water (5×10 mL) and brine (20 mL)
- dry with materialThe solution was dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7d18eac6239341a483c1a1a9b374e464
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138530B2
Reaction notes
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