Diisopropylethylamine → HCID 22854322, compound

HRID 1647182Notes

Reaction equation

HRID 1647182 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][CH2:53][O:54][NH2:55])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1.ClCCl>[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:55][O:54][CH2:53][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

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 202939Hydroxylamine, O-phenethyl-, hydrochlorideHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 22854322HCID 22854322, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

9-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol), O-(2-phenylethyl)hydroxylamine hydrochloride (0.70 g, 4.0 mmol) and diisopropylethylamine (0.95 g, 7.4 mmol) were dissolved in 1,4-dioxan (40 ml) and heated at reflux for 3 days. After cooling the reaction mixture was diluted with dichloromethane (50 ml) and washed with water (2×30 ml). The organic phase was dried (MgSO4). Flash chromatography on a silica gel column, eluting with heptane/ethyl acetate (1/1) gave the desired product as a foam (1.54 g, 66%), 1H NMR (DMSO-d6)γ 3.05 (2H, t, --OCH2 --), 4.19 (2H, t,--CH2Ph), 4.70 (1H, dd, H-5'a), 4.80 (1H, dd, H-5'b), 4.90 (1H, dd, H-4'), 5.22 (1H, t, H-3'), 6.39 (1H, t, H-2'), 6.59 (1H, d, H-1'), 8.51 (1H, s H-8).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 days
  3. temperatureAfter cooling the reaction mixture
  4. washwashed with water (2×30 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. washFlash chromatography on a silica gel column, eluting with heptane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-0c278747c58449bd933b7f0a4e943a87
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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