4-Toluenesulfonyl chloride → HCID 178501352, compound

HRID 1728475Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[NH:8][C:7](=[O:9])[C@H: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:4].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:47]1([CH3:57])[CH:52]=[CH:51][C:50]([S:53](Cl)(=[O:55])=[O:54])=[CH:49][CH:48]=1>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[N:8]([S:53]([C:50]2[CH:51]=[CH:52][C:47]([CH3:57])=[CH:48][CH:49]=2)(=[O:55])=[O:54])[C:7](=[O:9])[C@H: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:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:4]

Participants

Conditions

Temperature: -20 °C

Procedure

To a -78° C. THF (5 mL) solution of compound 7 (4.36 mg, 0.67 mmol) was added 1N THF solution of sodium bis(trimethylsilyl)amide (0.67 mL, 0.67 mmol), and the resultant solution was stirred for 15 min. p-Toluenesulfonyl chloride (134 mg, 0.70 mmol) was added, and the mixture was stirred at -78° C. for 4 h and at -20° C. for 21/2 days. The reaction mixture was partitioned between EtOAc and H2O. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (Et2O:hexane/3:2) to afford 210 mg (48%) of the title product.

Workup

customTo a -78° C
additionwas added
customThe reaction mixture was partitioned between EtOAc and H2O
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated
customThe residue was purified by silica gel chromatography (Et2O:hexane/3:2)

Sources & evidence

ORD record: ord-fcf94f0de3cd436fa021e9ac083daa53
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326863

Reaction notes

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