Ammonia → HCID 9800309, compound

HRID 1647183Notes

Reaction equation

[CH:1]1([O:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:16][C@@H:17]1[C@H:21]([O:22]C(=O)C2C=CC=CC=2)[C@@H:20]([CH2:31][O:32]C(=O)C2C=CC=CC=2)[O:19][C@H:18]1[N:41]1[CH:49]=[N:48][C:47]2[C:42]1=[N:43][C:44]([Cl:51])=[N:45][C:46]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:51][C:44]1[N:45]=[C:46]([NH:7][O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:47]2[N:48]=[CH:49][N:41]([C:42]=2[N:43]=1)[C@@H:18]1[O:19][C@H:20]([CH2:31][OH:32])[C@@H:21]([OH:22])[C@H:17]1[OH:16]

Participants

Reactant 3

HCID 222Ammonia

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

HCID 14326481O-Cyclopentylhydroxylamine

Product 1

HCID 9800309HCID 9800309, compound

Procedure

The title compound was prepared according to method A as described in example 6 by reacting O-cyclopentylhydroxylamine (prepared by the overall procedure described in example 5) (0.78 g, 5.67 mmol) with 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (3.0 g, 4.74 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro-N-cyclopentyloxyadenosine (0.11 g) (after column chromatography) as a solid, mp 116°-119° C., 1H NMR (DMSO-d6)γ 1.50-1.80 (8H, m, --CH2CH2CH2CH2 --), 3.52-3.58 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.94 (1H, q, H-4'), 4.13 (1H, q, H-3'), 4.51 (1H, q, H-2'), 4.57 (1H, br m,--OCH--), 5.06 (1H, t, 5'-- OH), 5.22, 5.50 (2H, 2d, 2'-and 3'--OH), 5.86 (1H, d, H-1'), 8.46 (1H, s, H-8), 11.40 (1H, s, N-H).

Workup

customThe title compound was prepared
customprepared by the overall procedure

Sources & evidence

ORD record: ord-7110fda1c5854dfa8ffb444441c2ab3b
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05430027

Reaction notes

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