HCID 178521052, compound → HCID 178521051, compound

HRID 1976544Notes

Reaction equation

HRID 1976544 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-3b7569a727344e75af4ac5f6b24476eb
Source dataset
uspto-grants-2001_05
Patent number
US06228847B1

Reaction notes

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