Propionyl chloride → N-[(1S,2R,3S,4R)-4-(6-amino-2-chloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide trifluoroacetate
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:24])=[N:18][C:19]=3[NH2:23])[C@H:11]([OH:25])[C@@H:10]1[OH:26].C(N(C(C)C)CC)(C)C.[C:36](Cl)(=[O:39])[CH2:37][CH3:38]>C1COCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:23][C:19]1[N:18]=[C:17]([Cl:24])[N:16]=[C:15]2[C:20]=1[N:21]=[CH:22][N:14]2[C@@H:12]1[CH2:13][C@H:9]([NH:8][C:36](=[O:39])[CH2:37][CH3:38])[C@@H:10]([OH:26])[C@H:11]1[OH:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(1S,2R,3S,5R)-3-Amino-5-(6-amino-2-chloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate (intermediate for preparing Example 1) (20 mg, 39 μmol) and diisopropylethylamine (25 mg, 190 μmol) are placed in a flask with dry THF (1 ml). Propionyl chloride (3.6 mg, 39 μmol) is added and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 3 hours. The solvent is removed in vacuo and the title compound is obtained, which can be purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water −0.1% TFA). 1H nmr (MeOD, 400 MHz); 8.10 (s, 1H), 4.75 (m, 1H), 4.60 (m, 1H), 4.20 (m, 1H), 4.00 (m, 1H), 3.75 (m, 1H), 3.25 (m, 1H), 2.85 (m, 1H), 2.40 (q, 2H), 2.10 (m, 1H), 1.20 (t, 3H), MS (ES+) m/e 341 (MH+).
Workup
- customThe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-71bcbd3d7465426d9da29cba9a2713b6
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318750B2
Reaction notes
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