Potassium Carbonate → HCID 178456833, compound

HRID 1854245Notes

Reaction equation

HRID 1854245 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]=[CH2:22])[S:10]2)[C@H:6]1[O:23]C(=O)C)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[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)[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178456832HCID 178456832, compound

Product 1

HCID 178456833HCID 178456833, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5R,6S,7R)-5-(acetoxymethyl)-2-(allylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (0.281 g, 0.73 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 crude material was purified via flash column chromatography (DCM:MeOH, 5:2) providing (5R,6S,7R)-2-(allylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (31) (0.048 g, 18% yield). 1H NMR: (500 MHz, methanol-d4) δ 3.50 (dd, 1H, J=5.5, 8.9 Hz), 3.6-3.7 (m, 2H), 3.81 (d, 1H, J=10.7 Hz), 3.87-3.95 (m, 3H), 4.09 (t, 1H, J=6.2 Hz), 5.15 (d, 1H, J=10.3 Hz), 5.25 (d, 1H, J=17.2 Hz), 5.88-5.96 (m, 1H), 6.36 (d, 1H, J=6.4 Hz). 13C NMR (125 MHz, methanol-d4) δ: 39.23, 61.80, 69.52, 73.52, 74.51, 75.39, 90.67, 161.87, 165.33.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified via flash column chromatography (DCM:MeOH, 5:2)

Sources & evidence

ORD record
ord-c18ebc0aaa8f4c95a5dcbcc7602a6818
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

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