Benzoyl chloride → HCID 131721217, compound

HRID 443006Notes

Reaction equation

HRID 443006 reaction equation
[C:1]([O:6][CH:7]([CH:30]=[CH2:31])[C@H:8]1[O:12][C@@H:11]([N:13]2[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:10][C@@H:9]1[O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])([O:3][CH2:4][CH3:5])=[O:2].[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:6][CH:7]([CH:30]=[CH2:31])[C@H:8]1[O:12][C@@H:11]([N:13]2[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[N:16]([C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:14]2=[O:15])[CH2:10][C@@H:9]1[O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 21309190HCID 21309190, compound

Product 1

HCID 131721217HCID 131721217, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5'-O-carbethoxy-5'-vinyl-3'-O-t-butyldimethylsilyl thymidine (1.7 g) in 20 ml of pyridine was added benzoyl chloride (2.5 eq.) and diisopropyl-ethylamine (95.0 eq.) and the resulting mixture was stirred for 15 hours. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate followed by brine, and the organic layer was then dried over sodium sulfate. The title compound was purified by flash chromatography using 20% ethyl acetate/hexane.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialthe organic layer was then dried over sodium sulfate
  3. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-85a57f8e286d4931b02dc0027ab5f5f4
Source dataset
uspto-grants-1999_04
Patent number
US05892024

Reaction notes

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