Ethanamine, 2,2,2-trifluoro- → HCID 14078937, compound

HRID 2194660Notes

Reaction equation

HRID 2194660 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10](N=C=S)[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7](COC(=O)C)[O:6]1)(=[O:3])[CH3:2].FC(F)(F)CN>CC#N>[C:1]([O:4][CH:5]1[CH2:10][CH:9]([O:14][C:15](=[O:17])[CH3:16])[CH:8]([O:18][C:19](=[O:21])[CH3:20])[CH2:7][O:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 14130735(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate

Product 1

HCID 14078937HCID 14078937, compoundYield 153.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (0.56 g, 1.44 mmol) in CH3CN, was added neat 2,2,2-trifluoroethylamine (0.236 g, 1.74 mmol), dropwise. The reaction was stirred at room temperature until complete by TLC (3 h). The reaction was quenched with saturated aqueous NaHCO3 (15 mL). The aqueous layer was then extracted three times with DCM, and the organic layers were combined, dried with MgSO4, filtered and concentrated. The concentrated mixture was purified via flash column chromatography in a solvent system of 1:1 EtOAc and hexanes, providing (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3,2,2,2-trifluoroethyl)thioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate (0.576 g, 81% yield). 1H NMR (500 MHz, CDCl3) δ 2.00 (6H, s), 2.04 (s, 3H), 3.87-3.90 (m, 1H), 4.03-4.11 (m, 1H), 4.20-4.26 (m, 2H), 4.36 (s, 1H), 5.07 (t, 1H, J=9.6 Hz), 5.27 (t, 1H, J=9.8 Hz), 5.73 (d, 1H, J=8.5 Hz), 6.75 (s, 2H).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (15 mL)
  2. extractionThe aqueous layer was then extracted three times with DCM
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrated mixture was purified via flash column chromatography in a solvent system of 1:1 EtOAc and hexanes

Sources & evidence

ORD record
ord-42b84d1691fb45c0a253e0334141d38c
Source dataset
uspto-grants-2012_12
Patent number
US08334310B2

Reaction notes

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