Potassium Carbonate → HCID 178521054, compound

HRID 2194661Notes

Reaction equation

HRID 2194661 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][C:21]([F:24])([F:23])[F:22])[S:10]2)[C@H:6]1[O:25]C(=O)C)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[OH:15][CH2:14][C@H:13]1[O:12][CH:11]2[CH:7]([N:8]=[C:9]([NH:19][CH2:20][C:21]([F:24])([F:22])[F:23])[S:10]2)[C@@H:6]([OH:25])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178476342HCID 178476342, compound

Product 1

HCID 178521054HCID 178521054, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5R,6S,7R)-5-(acetoxymethyl)-2-(2,2,2-trifluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (0.328 g, 0.776 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 h). The reaction was filtered and then concentrated in vacuo. The final reaction mixture was purified via flash column chromatography with a solvent system of 5:1 DCM and MeOH, providing (5R,6S,7R)-5-(hydroxymethyl)-2-(2,2,2-trifluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (39) (0.110 g, 47% yield). 1H NMR (500 MHz, methanol-d4) δ 3.47-3.50 (m, 1H), 3.61-3.69 (m, 2H), 3.81 (d, 1H, J=11.8 Hz), 3.92 (m, 3H), 4.03 (s, 1H), 4.10 (q, 1H, J=6.9 Hz), 6.35 (d, 1H, J=6.0 Hz). 13C NMR (125 MHz, methanol-d4) δ 61.94, 69.79, 74.31, 75.35, 123.82, 126.04, 175.25, 225.56.

Workup

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

Sources & evidence

ORD record
ord-1010de28198d4f9a8634cf7afcf78c4c
Source dataset
uspto-grants-2012_12
Patent number
US08334310B2

Reaction notes

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