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

HRID 2274448Notes

Reaction equation

HRID 2274448 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-0b592b44bd684c53afd438aded317c0a
Source dataset
uspto-grants-2015_09
Patent number
US09126971B2

Reaction notes

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