Ammonia → HCID 54568194, compound

HRID 1647185Notes

Reaction equation

HRID 1647185 reaction equation
[CH:1]1([O:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C([O:21][C@@H:22]1[C@H:26]([O:27]C(=O)C2C=CC=CC=2)[C@@H:25]([CH2:36][O:37]C(=O)C2C=CC=CC=2)[O:24][C@H:23]1[N:46]1[CH:54]=[N:53][C:52]2[C:47]1=[N:48][C:49]([Cl:56])=[N:50][C:51]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:56][C:49]1[N:50]=[C:51]([NH:12][O:11][CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[C:52]2[N:53]=[CH:54][N:46]([C:47]=2[N:48]=1)[C@@H:23]1[O:24][C@H:25]([CH2:36][OH:37])[C@@H:26]([OH:27])[C@H:22]1[OH:21]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 11355663HCID 11355663, compoundHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 54568194HCID 54568194, compoundYield 15%

Procedure

The title compound was prepared according to method B as described in examples 4 and 5 by reacting O-[1,2,3,4-tetrahydronaphth-1-yl)hydroxylamine (prepared by the procedure described in example 6) (0.35 g, 2.0 mmol) with 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.0 g, 1.58 mmol) and debenzoylating the purified product using methanolic ammonia to provide the title 2-chloro-N-(1,2,3,4-tetrahydronaphth-1-yloxy)adenosine (0.10 g, 15%) (after column chromatography) as a colourless foam (a mixture of diastereoisomers), 1H NMR (DMSO-d6)γ 1.65 - 2.85 (6H, m,--CH2CH2CH2 --), 3.53-3.61 (1H, m, H-5'a), 3.64-3.70 (1H, m, H-5'b), 3.94 (1H, br d, H-4'), 4.16 (1H, br d, H-3'), 4.53 (1H, q, H-2'), 5.07 (2H, m, 5'-OH and OCH--), 5.26, 5.53 (2H, 2d, 2'- and 3'-OH), 5.88 (1H, d, H-1'), 7.13-7.30 (3H, m, Ar-H), 7.88-7.96 (1H, m, Ar-H), 8.52 (1H, s, H-8), 11.60 (1H, br s, N-H). HPLC retention time 20.71 and 20.95 min (gradient elution over 25 min.; 25-45% acetonitrile/0.1M.

Workup

  1. customThe title compound was prepared
  2. customprepared by the procedure

Sources & evidence

ORD record
ord-1cf8fd9c39714b7d90eb8e8cece81517
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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