Potassium Carbonate → HCID 178521055, compound

HRID 1854249Notes

Reaction equation

HRID 1854249 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([CH2:14][O:15]C(=O)C)[O:12][CH:11]2[CH:7]([N:8]=[C:9]([NH:19][CH2:20][CH:21](F)[F:22])[S:10]2)[C@H:6]1[O:24]C(=O)C)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[F:22][CH2:21][CH2:20][NH:19][C:9]1[S:10][CH:11]2[O:12][C@H:13]([CH2:14][OH:15])[C@@H:5]([OH:4])[C@H:6]([OH:24])[CH:7]2[N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178476343HCID 178476343, compound

Product 1

HCID 178521055HCID 178521055, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5R,6S,7R)-5-(acetoxymethyl)-2-(2,2-difluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (0.209 g, 0.51 mmol) was dissolved in anhydrous MeOH. Solid K2CO3 was added to the solution until it was basic, and the reaction was stirred at room temperature (1.5 h). The reaction was filtered and then concentrated in vacuo. The resulting oil was purified via flash column chromatography with a solvent system of 5:1 DCM and MeOH, providing (5R,6S,7R)-2-(2-fluoroethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (37) (0.106 g, 74% yield),1H NMR (500 MHz, methanol-d4) δ 3.26-3.27 (m, 1H), 3.43-3.46 (m, 1H), 3.51-3.56 (m, 2H), 3.58-3.61 (m, 1H), 3.74 (dd, 1H, J=2.3, 11.9 Hz), 3.93 (t, 1H, J=5.4 Hz), 4.08 (t, 1H, J=6.0 Hz), 6.01 (tt, 1H, J=4.3, 56.4 Hz), 6.34 (d, 1H, J=6.4 Hz). 13C NMR (125 MHz, methanol-d4) δ 58.84, 69.85, 74.23, 75.17, 90.09, 114.19 (t, JC-F=241 Hz), 161.92.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was purified via flash column chromatography with a solvent system of 5:1 DCM and MeOH

Sources & evidence

ORD record
ord-a91fca39c9b2489384859cad46b77f3b
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

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