Pyridine, hydrofluoride (1:1) → Benzyloxymethyl-3'-O-benzoylthymidine

HRID 1489458Notes

Reaction equation

HRID 1489458 reaction equation
[CH2:1]([O:8][CH2:9][C@@:10]1([N:43]2[CH:51]=[C:49]([CH3:50])[C:47](=[O:48])[NH:46][C:44]2=[O:45])[O:42][C@H:22]([CH2:23][O:24][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:12]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.F>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][CH2:9][C@@:10]1([N:43]2[CH:51]=[C:49]([CH3:50])[C:47](=[O:48])[NH:46][C:44]2=[O:45])[O:42][C@H:22]([CH2:23][OH:24])[C@@H:12]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 131719889Benzyloxymethyl-3'-O-benzoyl-5'-O-tert-butyldiphenylsilylthymidine

Product 1

HCID 86750437Benzyloxymethyl-3'-O-benzoylthymidineYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The silyl ether 4 (96.0 g, 136.4 mmol) in THF (600 mL) was treated with hydrogen fluoride-pyridine (70% HF in pyridine, 30 mL) at 0° C. for 4 h under a N2 atmosphere. The resultant mixture was diluted with AcOEt (600 mL) and washed with H2O (2×300 mL). the organic layer was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by silica gel column chromatography (CH2 Cl2 /AcOEt 10:1) to give 61.6 g (97%) of 5 as a white solid. Rf (CH2Cl2 /AcOEt 10:1) 0.29.

Workup

  1. washwashed with H2O (2×300 mL)
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated at reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CH2 Cl2 /AcOEt 10:1)

Sources & evidence

ORD record
ord-c26967c83419409cb3925dab1655528b
Source dataset
uspto-grants-1997_10
Patent number
US05677437

Reaction notes

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