Trifluoroacetic acid → HCID 14130750, compound

HRID 1396233Notes

Reaction equation

[C:1]([O:4][CH2:5][C@@H:6]1[O:11][CH:10](CC([O-])=O)[C@H:9]([N:16]=[C:17]=[S:18])[C@H:8](CC([O-])=O)[C@@H:7]1CC([O-])=O)(=[O:3])[CH3:2].[CH2:27]([NH2:30])[CH2:28][CH3:29].F[C:32](F)(F)[C:33]([OH:35])=[O:34]>ClCCl>[C:33]([O:35][C@@H:7]1[C@@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:11][C@H:10]2[C@H:9]([N:16]=[C:17]([NH:30][CH2:27][CH2:28][CH3:29])[S:18]2)[C@H:8]1[O:4][C:1](=[O:3])[CH3:2])(=[O:34])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyltriacetate (59 g, 151 mmol) in dichloromethane (500 mL) was added propan-1-amine (9.4 g, 159 mmol) dropwise with stirring at 0° C. After stirred for 1 h, the reaction solution was treated with trifluoroacetic acid (130 g, 1.34 mol) overnight at room temperature. The reaction mixture was washed with saturated sodium bicarbonate (300 mL), dried over anhydrous 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 14 as a yellow oil (50 g, 84%). (ES, m/z): [M+H]+ 388.9; 1H NMR (300 MHz, CDCl3) δ 6.14-6.16 (d, J=6.6 Hz, 1H), 5.33-5.35 (m, 1H), 5.05-5.19 (m, 1H), 4.85-4.89 (m, 1H), 4.27-4.30 (m, 1H), 4.08 (s, 2H), 3.75-3.81 (m, 1H), 3.06-3.28 (m, 2H), 1.97-2.04 (m, 9H), 1.49-1.58 (m, 2H), 0.82-0.91 (m, 3H).

Workup

stirringAfter stirred for 1 h
washThe reaction mixture was washed with saturated sodium bicarbonate (300 mL)
dry with materialdried over anhydrous 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-a51808f80de540d384bd278c68d7d981
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901087B2

Reaction notes

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