Pivaloyl chloride → HCID 178475410, compound
Reaction equation
[C:1]([O:4][CH:5]1[NH:8][C:7](=[O:9])[CH:6]1[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:47](Cl)(=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49]>C1COCC1>[C:1]([O:4][CH:5]1[N:8]([C:47]([C:48]([CH3:51])([CH3:50])[CH3:49])=[O:52])[C:7](=[O:9])[CH:6]1[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a -78° C. THF (6 mL) solution of compound 13 (trans:cis ratio, 2:1, 600 mg; 1.2 mmol) was added 1N THF solution of sodium bis(trimethylsilyl)amide (1.2 mL, 1.2 mmol), and the resulting solution was stirred for 15 min. Pivaloyl chloride (150 mg, 1.24 mmol) was added, and the solution was stirred for 30 min at -78° C. and for 1.5 h at room temperature. The reaction mixture was partitioned between pH 4.0 aqueous buffer and ether. The organic phase was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (1:1/Et2O:hexane) to afford 300 mg (43%) of the title product as a mixture of trans and cis (3:2) isomers.
Workup
- customTo a -78° C
- stirringthe solution was stirred for 30 min at -78° C. and for 1.5 h at room temperature
- customThe reaction mixture was partitioned between pH 4.0 aqueous buffer
- dry with materialThe organic phase was dried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (1:1/Et2O:hexane)
Sources & evidence
- ORD record
- ord-f168c186810f4dce936ca0972beea46d
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05175283
Reaction notes
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