HCID 178521052, compound → HCID 178521051, compound

HRID 133486Notes

Reaction equation

HRID 133486 reaction equation
O[C:2]1[NH:7][C:6]2=[C:8]([C@@H:11]3[NH:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[CH:9]=[N:10][C:5]2=[C:4]([OH:20])[N:3]=1>FC(F)(F)C(O)=O>[OH:20][C:4]1[N:3]=[CH:2][NH:7][C:6]2=[C:8]([C@@H:11]3[NH:19][C@H:16]([CH2:17][OH:18])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[CH:9]=[N:10][C:5]=12

Participants

3

Reactant 1

HCID 178521052HCID 178521052, compound

Product 1

HCID 178521051HCID 178521051, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from Example 1.6 (66 mg) in trifluoroacetic acid (3 ml) was allowed to stand at room temperature overnight. The solution was concentrated and a solution of the residue in water was washed (×2) with chloroform and then evaporated. The residue was dissolved in methanol and treated with Amberlyst A21 base resin until the solution was pH˜7. The solids and solvent were removed and the residue was dissolved in water, treated with excess aqueous HCl and then lyophilized. Trituration of the residue with ethanol gave (1S)-1,4-dideoxy-1-C-(4-hydroxypyrrolo[3,2-d]pyrimidin-7-yl)-1,4-imino-D-ribitol (7) hydrochloride salt as a white solid (25 mg). Recrystallised from 90% ethanol, the crystalline solid darkened but did not melt below 300° C. NMR (300 MHz, D2O with DCl, δ ppm): 13C (relative to internal acetone at 33.2 ppm) 58.1 (C-1′), 61.4 (C-5′), 68.8 (C-4′), 73.3 (C-3′), 76.7 (C-2′), 107.5 (q), 121.4 (q), 133.5 (C-2), 135.0 (q), 148.0 (C-6) and 155.4 (q); 1H (relative to internal acetone at 2.20 ppm), 3.90 (H-4′), 3.96 (m, H-5′,5″), 4.44 (dd, H-3′, J2′,3′ 5.4 Hz, J3′,4′ 3.2 Hz), 4.71 (dd, J1′,2′ 9.0 Hz, H-2′), 5.00 (d, H-1′), 8.00 (s, H-6) and 9.04 (s, H-2).

Workup

  1. concentrationThe solution was concentrated
  2. washa solution of the residue in water was washed (×2) with chloroform
  3. customevaporated
  4. dissolutionThe residue was dissolved in methanol
  5. additiontreated with Amberlyst A21 base resin until the solution
  6. customThe solids and solvent were removed
  7. dissolutionthe residue was dissolved in water
  8. additiontreated with excess aqueous HCl

Sources & evidence

ORD record
ord-8b216ab16acc4530832d519aa8f2365b
Source dataset
uspto-grants-2008_06
Patent number
US07390890B2

Reaction notes

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