Triethylamine → HCID 22877227, compound

HRID 1379637Notes

Reaction equation

HRID 1379637 reaction equation
[NH2:1][C@H:2]([CH3:5])[CH2:3][OH:4].C([O:14][C@@H:15]1[C@H:19]([O:20]C(=O)C2C=CC=CC=2)[C@@H:18]([CH2:29][O:30]C(=O)C2C=CC=CC=2)[O:17][C@H:16]1[N:39]1[CH:47]=[N:46][C:45]2[C:40]1=[N:41][C:42]([Cl:49])=[N:43][C:44]=2Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>O1CCOCC1>[Cl:49][C:42]1[N:43]=[C:44]([NH:1][C@H:2]([CH3:5])[CH2:3][OH:4])[C:45]2[N:46]=[CH:47][N:39]([C:40]=2[N:41]=1)[C@@H:16]1[O:17][C@H:18]([CH2:29][OH:30])[C@@H:19]([OH:20])[C@H:15]1[OH:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 22877227HCID 22877227, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-2-Amino-1-propanol (0.23 g, 3.0 mmol), 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.7 g, 2.7 mmol) and triethylamine (0.30 g, 3.0 mmol) were dissolved in dioxan (20 ml) and stirred for 200 h at room temperature. Following purification by column chromatography, the resultant 2',3',5'-tri- O-benzoyl-2-chloro- N-[(R)-1-hydroxy-2-propyl]adenosine was deprotected using methanolic ammonia to provide the title 2-chloro- N-[(R)-1-hydroxy-2-propyl]adenosine as an amorphous foam (0.5 g, 54%), 1H NMR (DMSO-d6)δ 1.17 (3H, d, --CH3), 3.35-3.72 (4H, m, H-5'a, H-5'b and --CH2 --), 3.96 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.52 (1H, dd, H-2'), 5.08 (1H, t, 5'-OH), 5.22, 5.49 (2H, 2d, 2' and 3'-OH), 5.83 (1H, d, H-1'), 8.0 (1H, d, N--H) 8.40 (1H, s, H-8).

Workup

  1. custompurification by column chromatography

Sources & evidence

ORD record
ord-19f450d0811142c1ac06c7ec43f6e3af
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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