Potassium Carbonate → HCID 178456833, compound

HRID 2194656Notes

Reaction equation

HRID 2194656 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-c96509c386bd4d34b92ef0baf7f898bc
Source dataset
uspto-grants-2012_12
Patent number
US08334310B2

Reaction notes

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