Pivaloyl chloride → HCID 178475410, compound

HRID 1728498Notes

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

Conditions

Temperature: -78 °C

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 resultant 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
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-3a87327e9b354316bbb80e0696b06b50
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326863

Reaction notes

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