Potassium Carbonate → HCID 178521055, compound

HRID 1854247Notes

Reaction equation

HRID 1854247 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][CH2:21][F:22])[S:10]2)[C@H:6]1[O:23]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:23])[CH:7]2[N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178476344HCID 178476344, compound

Product 1

HCID 178521055HCID 178521055, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5R,6S,7R)-5-(acetoxymethyl)-2-(2-fluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (0.074 g, 0.19 mmol) was dissolved in anhydrous MeOH. 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 crude material 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 (35) (0.045 g, 90% yield). 1H NMR (500 MHz, methanol-d4) δ 3.47-3.67 (m, 5H), 3.78 (dd, 1H, J=2.1, 11.8 Hz), 3.92 (t, 1H, J=5.6 Hz), 4.06 (t, 1H, J=6.1 Hz), 4.40-4.50 (m, 1H), 4.50-4.56 (m, 1H), 6.31 (d, 1H, J=6.4 Hz). 13C NMR (125 MHz, methanol-d4) δ 62.02, 69.93, 74.41, 75.15, 81.31, 82.64, 89.84, 89.87, 162.00.

Workup

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

Sources & evidence

ORD record
ord-01bb900f757649f89aa734af72868a83
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

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