Diisopropylethylamine → HCID 22854324, compound

HRID 1647179Notes

Reaction equation

HRID 1647179 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:12][C@H:11]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][C:37]([Cl:44])=[N:38][C:39]=2Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:46]1([CH2:52][O:53][NH2:54])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[C:1]([O:9][C@@H:10]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:12][C@H:11]1[N:34]1[C:35]2[N:36]=[C:37]([Cl:44])[N:38]=[C:39]([NH:54][O:53][CH2:52][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]=2[N:41]=[CH:42]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 22854324HCID 22854324, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(This example was also prepared by general method A). 9-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol), O-(phenylmethyl)hydroxylamine hydrochloride (0.77 g, 4.8 mmol) and diisopropylethylamine (1.03 g, 8.0 mmol) were dissolved in dioxan (50 ml). The reaction mixture was heated at reflux for 20 h, filtered and evaporated in vacuo. The crude product was coevaporated with dichloromethane and crystallised from a mixture of dichioromethane and methanol to provide the title compound (1.0 g, 43%), as white crystals, mp 115°-119° C., 1H NMR (CDCl3)γ 3.52-3.70 (2H, m, H-5'a and H-5'b) 3.95 (1H, d, H-4'), 4.15 (1H, dd, H-3'), 4.52 (1H, dd, H-2'), 5.00 (2H, s, CH2), 5.88 (1H, d, H-1'), 8.52 (1H, s, H-8).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customcrystallised from a mixture of dichioromethane and methanol

Sources & evidence

ORD record
ord-05cd006406d947ceb14df8d968b99d43
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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