Trifluoroacetic acid → HCID 14130746, compound

HRID 1396239Notes

Reaction equation

[Cl-].C(O[CH:6]1[C@H:11]([NH3+:12])[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=O)C.[CH3:26][N:27]=[C:28]=[S:29].C(N(CC)CC)C.C(O)(C(F)(F)F)=O>CC#N>[C:18]([O:17][C@@H:9]1[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7][C@H:6]2[C@H:11]([N:12]=[C:28]([NH:27][CH3:26])[S:29]2)[C@H:10]1[O:13][C:14](=[O:16])[CH3:15])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (3R,4R,5S,6R)-2,4,5-triacetoxy-6-(acetoxymethyl)-tetrahydro-2H-pyran-3-aminium chloride (100 g, 261 mmol) in CH3CN (1 L) was added methyl isothiocyanate (21 g, 287 mmol), triethylamine (29 g, 287 mmol). After stirred for 12 h at 60° C., the resulting solution was treated with TFA (110 g, 0.96 mol) at room temperature overnight, and then washed with saturated sodium bicarbonate (1 L). The organic layer was dried over magnesium sulfate and concentrated under vacuum to provide a residue, which was purified by silica gel column, eluted with 1% MeOH in dichloromethane to give compound 23 as a yellow oil (150 g, 87%). (ES, tri/z): [M+H]+ 360.9; 1H NMR (300 MHz, CDCl3) δ 6.31-6.33 (d, J=6.6 Hz, 1H), 5.41-5.48 (t, J=8.4 Hz, 1H), 4.97-5.00 (m, 1H), 4.31-4.37 (t, J=5.7 Hz, 1H), 4.21 (m, 2H), 3.97 (m, 1H), 2.99 (s, 3H), 2.00-2.20 (m, 9H).

Workup

washwashed with saturated sodium bicarbonate (1 L)
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under vacuum
customto provide a residue, which
customwas purified by silica gel column
washeluted with 1% MeOH in dichloromethane

Sources & evidence

ORD record: ord-a244aee5a096483b92bd00af56d34fdd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901087B2

Reaction notes

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