Triethylamine → HCID 86638177, compound

HRID 1854255Notes

Reaction equation

HRID 1854255 reaction equation
Cl.[CH3:2][O:3][NH2:4].[C:5]([O:8][C@H:9]1[C@H:14]([N:15]=[C:16]=[S:17])[C@@H:13]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]([O:22][C:23](=[O:25])[CH3:24])[C@@H:11]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:10]1)(=[O:7])[CH3:6].C(N(CC)CC)C>C(#N)C>[C:5]([O:8][C@H:9]1[C@H:14]([NH:15][C:16]([NH:4][O:3][CH3:2])=[S:17])[C@@H:13]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]([O:22][C:23](=[O:25])[CH3:24])[C@@H:11]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:10]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 14130735(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate

Product 1

HCID 86638177HCID 86638177, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of methoxyamine hydrochloride (180 mg, 2.16 mmol) in acetonitrile (7 mL) was added (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (560 mg, 1.44 mmol) followed by triethylamine (300 μL., 2.16 mmol). The mixture was stirred at room temperature for 2 h. Solvents were removed by concentration. The residue was purified by flash chromatography on silica gel (hexane/EtOAc 1:1) to give (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-methoxythioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white solid (545 mg, 87% yield). 1H NMR (500 MHz, CDCl3) δ 2.05 (s, 3H), 2.09 (s, 3H), 2.10 (s, 6H), 2.13 (s, 3H), 3.67 (s, 3H), 3.82-3.85 (m, 1H), 4.15 (dd, 1H, J=2.5, 12.5 Hz), 4.28 (dd, 1H, J=4.5, 12.5 Hz), 5.03 (dd, 1H, J=10.0, 13.0 Hz), 5.20-5.30 (m, 2H), 5.84 (d, 1H, J=8.5 Hz), 7.01 (d, 1H, J=10.0 Hz).

Workup

  1. customSolvents were removed by concentration
  2. customThe residue was purified by flash chromatography on silica gel (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-9945d60f0c544ba696ffd26ca81f7d58
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

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