HCID 22854555, compound → HCID 10022940, compound

HRID 1647514Notes

Reaction equation

HRID 1647514 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[N:34]1[C:49]2[N:48]=[C:47]([Cl:50])[N:46]=[C:38]([NH:39][N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[C:37]=2[N:36]=[CH:35]1)(=O)C1C=CC=CC=1>N>[Cl:50][C:47]1[N:46]=[C:38]([NH:39][N:40]2[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]2)[C:37]2[N:36]=[CH:35][N:34]([C:49]=2[N:48]=1)[C@@H:11]1[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

3

Reactant 1

HCID 22854555HCID 22854555, compound

Product 1

HCID 10022940HCID 10022940, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The above 2',3',5'-tri-O-benzoyl-2-chloro-N-(1-piperidinyl)adenosine (19.2 g, 27.5 mmol) was dissolved in methanolic ammonia (150 ml) (previously saturated at -10° C.) and stirred at room temperature for 18 hours. The precipitated benzamide was removed by filtration, and the filtrate was evaporated to a fawn oil, which was triturated with diethyl ether to provide the title compound (6.0 g, 57%) as a white foam, 1H NMR (400 MHz, Me2SO-d6) δ3.55 (1H, m, H-5'a), 3.66 (1H, m, H-5'b), 3.94 (1H, q, H-4'), 4.12 (1H, m, H-3'), 4.50 (1H, q, H-2'), 5.82 (1H, d, H-1'), 8.40 (1H, s, H-8); HPLC retention time 26.57 (gradient elution, 5-25% acetonitrile/0.1M pH 3.3 ammonium sulphate buffer: 214 nm detector); purity 99%.

Workup

  1. customThe precipitated benzamide was removed by filtration
  2. customthe filtrate was evaporated to a fawn oil, which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-8a066f29a6db4f78a8e5f47288a0a443
Source dataset
uspto-grants-1995_07
Patent number
US05432164

Reaction notes

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