Potassium Carbonate → (3aR,5R,6S,7R,7aR)-2-(2-fluoroethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

HRID 1396255Notes

Reaction equation

HRID 1396255 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([CH2:14][O:15]C(=O)C)[O:12][C@H:11]2[C@H: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][C@H:11]2[O:12][C@H:13]([CH2:14][OH:15])[C@@H:5]([OH:4])[C@H:6]([OH:23])[C@H:7]2[N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59153312[(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-(2-fluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate

Product 1

HCID 59153299(3aR,5R,6S,7R,7aR)-2-(2-fluoroethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diolYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-fluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (29 g, 74 mmol) in methanol (200 mL) was treated with potassium carbonate (1 g, 7 mmol) overnight at room temperature. The solids were collected by filtration and washed with dichloromethane (3×50 mL) to afford compound 67 as a white solid (18 g, 92%). (ES, m/z) [M+H]+ 266.9; 1H NMR (300 MHz, D2O) δ 6.21-6.23 (d, J=6.3 Hz, 1H), 4.55-4.59 (m, 1H), 4.40-4.44 (m, 1H), 4.10-4.14 (t, J=5.7 Hz, 1H), 3.95-3.98 (t, J=5.4 Hz, 1H), 3.70-3.75 (m, 1H), 3.40-3.62 (m, 5H).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with dichloromethane (3×50 mL)

Sources & evidence

ORD record
ord-122f49848fe74de49f3e2ad4bd1196d5
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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