HCID 178526947, compound → HCID 178521081, compound

HRID 1672519Notes

Reaction equation

HRID 1672519 reaction equation
O.[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[NH:8][CH:9]=[C:10]([C@@H:12]([OH:19])[C@H:13]([OH:18])[C@H:14]([OH:17])[CH2:15][OH:16])[N:11]=2)=[N:3]1>C(O)C>[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[NH:8][CH:9]=[C:10]([C@@H:12]([OH:19])[C@H:13]([OH:18])[C@H:14]([OH:17])[CH2:15][OH:16])[N:11]=2)=[N:3]1

Participants

3

Reactant 1

HCID 178526947HCID 178526947, compound

Product 1

HCID 178521081HCID 178521081, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
12.5 °C

Procedure

(1R,2S,3R)-1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol hydrate (726 g) was heated in 7200.0 g (10.0×) of ethanol for 3-3.5 h at 75-80° C., and then cooled slowly to 10-15° C. and stirred for 2-2.5 h at 10-15° C. The solids were filtered, washed with 726 g (1.0×) of ethanol and dried under vacuum for 20 hrs at 30-40° C. to yield 663 g of anhydrous (1R,2S,3R)-1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol as off-white solid. 1H NMR (DMSO-d6 with a drop of DCl, 400 MHz) δ 8.71 (t, J=0.8 Hz, 1H), 7.40 (s, 1H), 6.89 (t, J=0.8 Hz, 1H), 5.06 (d, J=1.2 Hz, 1H), 3.53-3.69 (m, 3H), 3.49-3.52 (m, 1H); 13C NMR (DMSO-d6 with a drop of DCl, 100 MHz) δ 163.2, 149.6, 139.0, 133.0, 118.5, 104.8, 73.4, 71.4, 65.2, 63.8; Elemental analysis: Found: C, 44.50; N, 15.77; H, 5.39. Calculated for C10H13N3O5: C, 47.06; N, 16.46; H, 5.13.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with 726 g (1.0×) of ethanol
  3. customdried under vacuum for 20 hrs at 30-40° C.

Sources & evidence

ORD record
ord-4981ff9659724c4f95f88fee17d80846
Source dataset
uspto-grants-2011_08
Patent number
US07998994B2

Reaction notes

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