p-Anisoyl chloride → HCID 9958543, compound

HRID 1060841Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=1)[O:15][C@@H:16]([CH3:23])[C:17]([O:19]CC=C)=[O:18])=[CH:8][C:7]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:6][CH:5]=2.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:42](Cl)(=[O:51])[C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1>O1CCCC1>[CH3:50][O:49][C:46]1[CH:47]=[CH:48][C:43]([C:42]([N:3]2[C:4]3[C:9](=[CH:8][C:7]([O:27][C:28]([F:30])([F:29])[F:31])=[CH:6][CH:5]=3)[C:10]([CH2:11][C:12]3[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=3)[O:15][C@@H:16]([CH3:23])[C:17]([OH:19])=[O:18])=[C:2]2[CH3:1])=[O:51])=[CH:44][CH:45]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Compound 5 (467 mg, 1.1 mmole) was dissolved in tetrahydrofuran (11 mL) and cooled to −78° C. Sodium bis(trimethylsilyl)amide 1.3 mL of a 1.0N solution in THF) was added and the reaction mixture was stirred for 10 minutes. p-Anisoyl chloride (221 mg, 1.3 mmole) was then added. The reaction was warmed to 0° C. then quenched with saturated ammonium chloride and diluted with ether (100 ml). The ether layer was washed with water (2×), brine (1×) and dried over sodium sulfate followed by filtration and evaporation of the filtrate giving the title compound after silica gel chromatography (490 mg, 79%).

Workup

temperatureThe reaction was warmed to 0° C.
customthen quenched with saturated ammonium chloride
additiondiluted with ether (100 ml)
washThe ether layer was washed with water (2×), brine (1×)
dry with materialdried over sodium sulfate
filtrationfollowed by filtration and evaporation of the filtrate

Sources & evidence

ORD record: ord-01339bdcb0a74836a6ea9c0f8bcc9148
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525083B2

Reaction notes

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