Imidazole → HCID 15747244, compound

HRID 2393713Notes

Reaction equation

HRID 2393713 reaction equation
[C:1]1(=[O:28])[N:5]([O:6][CH2:7][C@H:8]2[O:12][C@@H:11]([N:13]3[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]3=[O:15])[CH2:10][C@@H:9]2[OH:22])[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]12.[Si:29](Cl)([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N1C=CN=C1>CN(C=O)C>[Si:29]([O:22][C@@H:9]1[C@@H:8]([CH2:7][O:6][N:5]2[C:4](=[O:23])[C:3]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]3[C:1]2=[O:28])[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]1)([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 157472435'-O-phthalimidothymidine

Product 1

HCID 15747244HCID 15747244, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5'-O-phthalimidothymidine (8.54 g, 22 mmol), t-butyldiphenylsilylchloride (6.9 ml, 26.5 mmol), imidazole (3.9 g, 57.3 mmol) and dry DMF (130 ml) was stirred at room temperature for 16 h under argon. The reaction mixture was poured into ice-water (600 ml) and the solution was extracted with CH2Cl2 (2×400 ml). The organic layer was washed with water (2×250 ml) and dried (MgSO4). The CH2Cl2 layer was concentrated to furnish a gummy residue which on purification by silica gel chromatography (eluted with EtOAc:Hexanes; 1:1, v/v) furnished 12.65 g (92%) of 3'-O-(t-butyldiphenylsilyl)-5'-O-phthalimidothymidine as crystalline material (mp 172°-173.5° C.). 1M NMR (DMSO-d6) δ 11.31 (s, 1, NH), 7.83 (m, 4, ArH), 7.59 (m, 4, TBDPhH), 7.51 (s, 1, C6H), 7.37-7.45 (m, 6, TBDPhH), 6.30 (dd, 1, H1', J1',2' =8.8 Hz, J1',2" =5.6 Hz), 4.55 (m, 1, H4'), 4.15 (m, 1, H3'), 3.94-4.04 (m, 2, H5',5"), 2.06-2.13 (m, 2, H2',2"), 1.97 (s, 3, CH3), 1.03 (s, 9, C(CH3)3). Anal. Calcd. for C34H35O7N3Si: C, 65.26; H, 5.64; N, 6.71. Found: C, 65.00; H, 5.60; N, 6.42.

Workup

  1. extractionthe solution was extracted with CH2Cl2 (2×400 ml)
  2. washThe organic layer was washed with water (2×250 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationThe CH2Cl2 layer was concentrated
  5. customto furnish a gummy residue which
  6. customon purification by silica gel chromatography (
  7. washeluted with EtOAc

Sources & evidence

ORD record
ord-4029ea8023334e29b326121b3d4779b3
Source dataset
uspto-grants-1998_09
Patent number
US05808023

Reaction notes

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