Potassium Carbonate → HCID 67205091, compound

HRID 1396234Notes

Reaction equation

HRID 1396234 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][CH3:22])[S:10]2)[C@H:6]1[O:23]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:15][CH2:14][C@H:13]1[O:12][C@H:11]2[C@H:7]([N:8]=[C:9]([NH:19][CH2:20][CH2:21][CH3:22])[S:10]2)[C@@H:6]([OH:23])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14130750HCID 14130750, compound

Product 1

HCID 67205091HCID 67205091, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (100 g, 257 mmol) in methanol (800 mL) was added potassium carbonate (18 g, 130 mmol). The resulting solution was stirred overnight at 40° C. and then cooled down to 0° C. to yield a solid This was collected by filtration, washed with cold methanol and dried. The product 15 was obtained as a white solid (50 g, 74%). (ES, m/z): [M+H]+ 262.9; 1H NMR (300 MHz, D2O) δ 6.17-6.19 (d, J=6.3 Hz, 1H), 4.07-4.10 (m, 1H), 3.93-3.96 (m, 1H), 3.71-3.76 (m, 1H), 3.45-3.69 (m, 3H), 3.04-3.13 (m, 2H), 1.39-1.51 (m, 2H), 0.82-0.91 (m, 3H).

Workup

  1. temperaturecooled down to 0° C.
  2. customto yield a solid
  3. filtrationThis was collected by filtration
  4. washwashed with cold methanol
  5. customdried

Sources & evidence

ORD record
ord-3df94c2658c14e359b572202e2fde380
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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