Hydrochloric Acid → HCID 131717582, compound

HRID 466479Notes

Reaction equation

[C:1]([C:3](=[C:25]1[CH2:29][CH2:28][CH2:27][O:26]1)[C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].FC(F)(F)S([Cl:45])(=O)=O.[ClH:48]>C(OCC)(=O)C.C1COCC1>[C:1]([C:3](=[C:25]1[C:29]([Cl:45])([Cl:48])[CH2:28][CH2:27][O:26]1)[C:4]1[C:5]([CH2:21][CH:22]([CH3:23])[CH3:24])=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:12])([F:11])[F:13])#[N:2]

Participants

Conditions

Temperature: -70 °C

Procedure

A 100 mL round-bottomed flask was charged with 1.5 g (3.6 mmol) of the compound of Example 2 and 20 mL anhydrous THF. The solution was cooled to -70° C. and 3.6 mL sodium bis(trimethylsilyl)amide (1.0 M solution in THF) was added via syringe. After 5 minutes, 0.6 g (3.6 mmol) trifluoromethanesulfonyl chloride was added. After 15 minutes an additional 3.6 mL sodium bis(trimethylsilyl)amide was added followed by additional 0.6 g trifluoromethanesulfonyl chloride. After stirring one hour at -70° C., the reaction solution was poured into dilute HCl and extracted with ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, an filtered to give 1.5 g of crude orange oil. Chromatography using 20% ethyl acetate in hexanes yielded 0.42 g of the desired product as a yellow oil, a 24% yield. nD25 1.4920.

Workup

extractionextracted with ethyl ether
washThe combined organic layers were washed with brine
dry with materialdried over magnesium sulfate
filtrationan filtered
customto give 1.5 g of crude orange oil

Sources & evidence

ORD record: ord-a4adea0235cf40bf9d1817f095934420
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05156670

Reaction notes

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