HCID 22854552, compound → HCID 44323376, compound

HRID 1647518Notes

Reaction equation

HRID 1647518 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:34]2[N:33]=[C:32]([Br:35])[N:31]=[C:23]([NH:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:22]=2[N:21]=[CH:20]1)(=O)C>N>[Br:35][C:32]1[N:31]=[C:23]([NH:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[C:22]2[N:21]=[CH:20][N:19]([C:34]=2[N:33]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

3

Reactant 1

HCID 22854552HCID 22854552, compound

Product 1

HCID 44323376HCID 44323376, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The above 2',3',5'-tri-O-acetyl-2-bromo-N-(1-piperidinyl)adenosine was treated with methanolic ammonia (10 ml) (previously saturated at -10° C.) and stirred at room temperature for 16 hours after which time TLC investigation indicated that the starting material was consumed and a new product was present [rf 0.24 (SiO2, ethyl acetate/methanol (90/10)]. The reaction mixture was evaporated and the resultant residue was treated with water (25 ml) and the suspension was extracted with ethyl acetate (2×25 ml). The combined extracts were dried (MgSO4) and coevaporated with dichloromethane; 1H NMR (400 MHz, Me2SO-d6) δ3.54, 3.65 (2H, ABX, H-5'a and H-5'b), 3.94 (1H, q, H-4'), 4.12 (1H, m, H-3'), 4.50 (1H, m, H-2'), 5.82 (1H, d, H-1'), 8.38 (1H, s, H-8). HPLC retention time 14.25 (gradient elution, 5-25% acetonitrile/0.1M pH 3.3 ammonium sulphate buffer: 214 nm detector).

Workup

  1. customwas consumed
  2. customThe reaction mixture was evaporated
  3. additionthe resultant residue was treated with water (25 ml)
  4. extractionthe suspension was extracted with ethyl acetate (2×25 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. washHPLC retention time 14.25 (gradient elution, 5-25% acetonitrile/0.1M pH 3.3 ammonium sulphate buffer: 214 nm detector)

Sources & evidence

ORD record
ord-9c43fbb189184a819df1ef4608278d86
Source dataset
uspto-grants-1995_07
Patent number
US05432164

Reaction notes

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