HCID 69486922, compound → HCID 9903844, compound

HRID 722004Notes

Reaction equation

HRID 722004 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@:8]([CH3:24])([CH2:14][O:15]C(=O)C2C=CC=CC=2)[O:7][C@H:6]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][CH:28]=[N:29][C:30]=2[NH2:34])(=O)C>N>[CH3:24][C@:8]1([CH2:14][OH:15])[O:7][C@@H:6]([N:25]2[CH:33]=[N:32][C:31]3[C:26]2=[N:27][CH:28]=[N:29][C:30]=3[NH2:34])[C@H:5]([OH:4])[C@@H:9]1[OH:10]

Participants

3

Reactant 1

HCID 69486922HCID 69486922, compound

Product 1

HCID 9903844HCID 9903844, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 20 (970 mg, 2.08 mmol) in methanolic ammonia (previously saturated at −10° C.) (50 mL) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between methylene chloride (100 ml) and water (100 ml). The aqueous layer was washed with methylene chloride (2×100 mL), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (10–30%) in ethyl acetate] to afford pure 21 (554 mg, 95%). Crystallization from methanol/ethyl acetate gave 21 as a white solid. Mp: 96–97 (dec.); 1H-NMR (DMSO-d6): δ 8.33 (s, 1H, H-2), 8.13 (s, 1H, H-8), 7.36 (brs, 2H, NH2), 5.84 (d, 1H, H-1′, J1′-2′=7.4 Hz), 5.69 (dd, 1H, OH-5′, J=4.2 Hz and J=7.8 Hz), 5.33 (d, 1H, OH-2′, J=6.6 Hz), 5.13 (d, 1H, OH-3′, J=4.4 Hz), 4.86 (m, 1H, H-2′), 4.04 (t, 1H, H-3′), 3.58–3.32 (m, 2H, H-5′ and H-5″), 1.15 (s, 3H, CH3); MS (matrix GT): FAB>0 m/z 563 (2M+H)+, 374 (M+G+H)+, 282 (M+H)+, 136 (B+2H)+, FAB<0 m/z 561 (2M−H)−, 280 (M−H)−, 134 (B)−.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between methylene chloride (100 ml) and water (100 ml)
  3. washThe aqueous layer was washed with methylene chloride (2×100 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-06d3268660a244298ca87fc25b03ad13
Source dataset
uspto-grants-2006_11
Patent number
US07138376B2

Reaction notes

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