Pyridine → HCID 21309190, compound

HRID 443005Notes

Reaction equation

HRID 443005 reaction equation
[CH:1]([CH:3]([OH:26])[C@H:4]1[O:8][C@@H:7]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:6][C@@H:5]1[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH2:2].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].N1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C>[C:28]([O:26][CH:3]([CH:1]=[CH2:2])[C@H:4]1[O:8][C@@H:7]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:6][C@@H:5]1[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])([O:30][CH2:31][CH3:32])=[O:29]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 21309194HCID 21309194, compound

Product 1

HCID 21309190HCID 21309190, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5'-vinyl-3'-O-t-butyldimethylsilyl thymidine (2.0 g) in 30 ml of methylene chloride was added ethyl chloroformate (6 eq.) and pyridine (12 eq.) and the resulting mixture was stirred for 2 hours. The mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, then with water (2×25 ml), and then with brine. Then the organic layer was dried. The title compound was purified by flash chromatography using 20% ethyl acetate/hexane.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. customThen the organic layer was dried
  3. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-1eca77e02aa848f297d51a09a68b637a
Source dataset
uspto-grants-1999_04
Patent number
US05892024

Reaction notes

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