HCID 86601631, compound → HCID 16087946, compound
Reaction equation
[CH3:1][NH:2][C:3]([C@@:5]1([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([Cl:33])=[N:19][C:20]=3[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([I:32])[CH:27]=2)[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[O:11]2)[CH2:7][S:6]1)=[O:4]>C(O)(=O)C>[CH3:1][NH:2][C:3]([C@@:5]1([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([Cl:33])=[N:19][C:20]=3[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([I:32])[CH:27]=2)[C@@H:12]([OH:11])[C@@H:8]([OH:9])[CH2:7][S:6]1)=[O:4]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
4 mL of 80% aqueous acetic acid solution were added to 42 mg (0.07 mmol) of (3aS,4R, 6aR)-4-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4-carboxylic acid methyl amide from the aforementioned Experimental Example 11, which was then stirred at 55° C. for 12 h. The reaction mixture was distilled under reduced pressure, and then the pH of the concentrate was adjusted to neutral by adding a saturated ammonia methanol solution. The concentrate was purified by silica gel column chromatography using the eluant (dichloromethane and methanol=7:1) to obtain 20 mg (yield: 52%) of (2R,3S,4R)-2-[2-chloro-6-(3-iodobenzylamino)purin-9-yl)-3,4-dihydroxytetrahydrothiophene-2-carboxylic acid methyl amide as white solids (see Table 1).
Workup
- distillationThe reaction mixture was distilled under reduced pressure
- additionby adding a saturated ammonia methanol solution
- customThe concentrate was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-4fa6ca9031de42249e2ed4c63bf97e3d
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199127B2
Reaction notes
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