2-Chlorotrityl chloride → HCID 68700549, compound

HRID 1818669Notes

Reaction equation

HRID 1818669 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16].[Cl:17][C:18]1[CH:37]=[CH:36][CH:35]=[CH:34][C:19]=1[C:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:17][C:18]1[CH:37]=[CH:36][CH:35]=[CH:34][C:19]=1[C:20]([NH:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 945242-Chlorotrityl chloride2×HCID 451827Uridine, 5'-amino-2',5'-dideoxy-

Product 1

HCID 68700549HCID 68700549, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

5′-Amino-2′,5′-dideoxyuridine (0.237 g, 1.04 mmol) was reacted with 2-chlorotrityl chloride (0.415 g, 1.33 mmol) in dry pyridine (5 mL) at 40° C. for 24 h. A second portion of 2-chlorotrityl chloride (0.198 g, 0.63 mmol) was added. After a further 2 h stirring at 40° C., the reaction was quenched with MeOH (2 mL). The reaction mixture was concentrated in vacuo and purified by flash column chromatography using an ISOLUTE Si column eluted with a gradient of 0→5% CH3OH in CHCl3. The fractions with Rf=0.17 (10% CH3OH/CHCl3) yielded the title compound as a white solid (85 mg, 16%).

Workup

  1. customthe reaction was quenched with MeOH (2 mL)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash column chromatography
  4. washeluted with a gradient of 0→5% CH3OH in CHCl3

Sources & evidence

ORD record
ord-f0d21cf4c9a648d88cf4eea650260c6a
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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