Imidazole → 1-[5-O-Benzoyl-2-deoxy-4-ethynyl-beta-D-threo-pentofuranosyl]thymine

HRID 215730Notes

Reaction equation

HRID 215730 reaction equation
[C:1]([O:9][CH2:10][C@@:11]1([C:33]#[C:34][Si](C)(C)C)[O:15][C@@H:14]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][C@H:12]1[O:25][Si](C(C)(C)C)(C)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.CC([Si](Cl)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C>CN(C=O)C>[C:1]([O:9][CH2:10][C@@:11]1([C:33]#[CH:34])[O:15][C@@H:14]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][C@H:12]1[OH:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 115269021-[5-O-Benzoyl-3-O-(t-butyldimethylsilyl)-2-deoxy-4-(trimethylsilyl)ethynyl-beta-D-threo-pentofuranosyl]thymine

Product 1

HCID 115887611-[5-O-Benzoyl-2-deoxy-4-ethynyl-beta-D-threo-pentofuranosyl]thymineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3 (10.35 g, 60.1 mmol), imidazole (8.18 g, 120.2 mmol), and TBDPSCl (15.6 ml, 60.1 mmol) in DMF (40 ml) was stirred for 16 h at room temperature under positive pressure of dry Ar. The mixture was partitioned between EtOAc and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The resulting syrupy residue was treated with MeOH (ca. 40 ml) to give the precipitated 4. This procedure was repeated further 3 times to give 4 (18.97 g, 77%) as a white solid.

Workup

  1. customThe mixture was partitioned between EtOAc and sat. aqueous NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. additionThe resulting syrupy residue was treated with MeOH (ca. 40 ml)
  5. customto give the
  6. customprecipitated 4

Sources & evidence

ORD record
ord-8ac37bfb6e1e4266b206f134bbb7b67c
Source dataset
uspto-grants-2012_06
Patent number
US08193165B2

Reaction notes

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