Triethylamine → HCID 22877228, compound

HRID 1379648Notes

Reaction equation

HRID 1379648 reaction equation
[C:1]1([S:7]([CH2:10][C@H:11]([NH2:13])[CH3:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:22][C@@H:23]1[C@H:27]([O:28]C(=O)C2C=CC=CC=2)[C@@H:26]([CH2:37][O:38]C(=O)C2C=CC=CC=2)[O:25][C@H:24]1[N:47]1[CH:55]=[N:54][C:53]2[C:48]1=[N:49][C:50]([Cl:57])=[N:51][C:52]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>O1CCOCC1>[Cl:57][C:50]1[N:51]=[C:52]([NH:13][C@H:11]([CH3:12])[CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])[C:53]2[N:54]=[CH:55][N:47]([C:48]=2[N:49]=1)[C@@H:24]1[O:25][C@H:26]([CH2:37][OH:38])[C@@H:27]([OH:28])[C@H:23]1[OH:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 54550950HCID 54550950, compound

Product 1

HCID 22877228HCID 22877228, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-1-Phenylsulphonyl-2-propylamine (0.4 g, 1.7 mmol) was reacted with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.7 g, 1.0 mmol) in dioxan (20 ml) in the presence of triethylamine (0.4 g, 4.3 mmol). The reaction mixture was stirred at room temperature for 48 h, heated at 60° C. for 4 h, cooled, filtered and evaporated. The product (after purification by flash chromatography) was debenzoylated with methanolic ammonia to provide the title 2-chloro- N-[(R)-1-phenylsulphonyl-2-propyl]adenosine (after column chromatography) as a foam (0.2 g, 24%), 1H NMR (DMSO-d6)δ 1.24 (3H, d, --CH3), 3.45 (1H, dd, --C--H), 3.53-3.61 (2H, m, H-5'a and --C--H), 3.64-3.71 (1H, m, H-5'b), 3.86 (1H, dd, --C--H), 3.97 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.53 (1H, m, H-2'), 5.09 (1H, t, 5'-OH), 5.23, 5.50 (2H, 2 d, 2' and 3'-OH), 5.83 (1H, d, H-1'), 7.45-7.82 (5H, m, Ar--H), 8.21 (1H, s, --N--H), 8.38 (1H, s, H-8).

Workup

  1. temperatureheated at 60° C. for 4 h
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated
  5. customThe product (after purification by flash chromatography)

Sources & evidence

ORD record
ord-9959ad1387e140b3be31d9a2398b7382
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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