(Diethylamino)sulfur trifluoride → HCID 46180112, compound

HRID 1793959Notes

Reaction equation

C(N(S(F)(F)[F:7])CC)C.[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH:17](O)[CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])(=[O:12])[CH3:11]>C(Cl)Cl.C(OCC)(=O)C>[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH:17]([F:7])[CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])(=[O:12])[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (diethylamino)-sulfur trifluoride (571 mg, 3.54 mmol) in CH2Cl2 was added the solution of acetic acid, 7-acetoxy-4-hydroxy-heptyl ester (403 mg, 1.74 mmol) in CH2Cl2 (10 ml) at −78° C. The resulting mixture was allowed to stir for 15 minutes at −78° C., 30 minutes at room temperature and then diluted with ethyl acetate (300 ml). The organic solution was washed with sat. NaHCO3, brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by column chromatography on silica gel, using 15% ethyl acetate in hexanes, gave the title compound (386 mg, 94%) as a colorless oil. 1H NMR (CDCl3) δ 1.55–1.83 (m, 8H), 2.05 (s, 6H), 4.05–4.15 (m, 4H), 4.39–4.63 (m, 1H); 13C NMR (CDCl3) δ 20.97, 24.42, 24.48, 31.51, 31.79, 64.03, 92.22, 94.45, 171.12; 19F NMR (CDCl3) δ −106.44–105.27(m); ES-MS m/z 257.3 (M+Na).

Workup

washThe organic solution was washed with sat. NaHCO3, brine
dry with materialdried over Na2SO4
customEvaporation of the solvent and purification of the residue by column chromatography on silica gel

Sources & evidence

ORD record: ord-3a1f432bd829491cad0db02a7d640d0f
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022717B2

Reaction notes

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