Hydrochloric Acid → HCID 131717581, compound

HRID 466478Notes

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

Participants

Conditions

Temperature: -70 °C

Procedure

A 100 mL round-bottomed flask was charged with 1.2 g (2.9 mmol) of the compound of Example 2 and 30 mL anhydrous THF and cooled to -70° C. Then 2.9 mL sodium bis(trimethylsilyl)amide (1.0 M solution in THF) was added. After 5 minutes, 0.48 g (2.9 mmol) trifluoromethanesulfonyl chloride was added. To the reaction mixture was added 0.25 g additional trifluoromethanesulfonyl chloride. The reaction mixture was poured into dilute HCl and extracted with ethyl ether. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 1.3 g of crude product. Chromatography using 15% ethyl acetate in hexanes yielded 0.34 g of the desired product, as a yellow oil, a 27% yield. nD25 1.4860.

Workup

extractionextracted with ethyl ether
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give 1.3 g of crude product

Sources & evidence

ORD record: ord-a0525e9a6b8f47b992c9904b3cb829ec
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05156670

Reaction notes

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